US2376380A - Preparation of amino pyrazolones - Google Patents
Preparation of amino pyrazolones Download PDFInfo
- Publication number
- US2376380A US2376380A US2376380DA US2376380A US 2376380 A US2376380 A US 2376380A US 2376380D A US2376380D A US 2376380DA US 2376380 A US2376380 A US 2376380A
- Authority
- US
- United States
- Prior art keywords
- hydrazine
- amino
- ethyl
- preparation
- pyrazolones
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
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- 238000002360 preparation method Methods 0.000 title description 14
- XSFKCGABINPZRK-UHFFFAOYSA-N 4-aminopyrazol-3-one Chemical class NC1=CN=NC1=O XSFKCGABINPZRK-UHFFFAOYSA-N 0.000 title description 12
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 28
- -1 AMINO Chemical class 0.000 description 22
- XBDQKXXYIPTUBI-UHFFFAOYSA-M propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 20
- 239000000203 mixture Substances 0.000 description 14
- 238000010438 heat treatment Methods 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
- HKOOXMFOFWEVGF-UHFFFAOYSA-N Phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 10
- 229940067157 phenylhydrazine Drugs 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- 125000003118 aryl group Chemical group 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 8
- 150000002429 hydrazines Chemical group 0.000 description 8
- 239000000376 reactant Substances 0.000 description 8
- XNINAOUGJUYOQX-UHFFFAOYSA-M 2-cyanobutanoate Chemical compound CCC(C#N)C([O-])=O XNINAOUGJUYOQX-UHFFFAOYSA-M 0.000 description 6
- KMVPXBDOWDXXEN-UHFFFAOYSA-N 4-nitrophenylhydrazine Chemical compound NNC1=CC=C([N+]([O-])=O)C=C1 KMVPXBDOWDXXEN-UHFFFAOYSA-N 0.000 description 6
- QDRKDTQENPPHOJ-UHFFFAOYSA-N Sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 6
- 125000000623 heterocyclic group Chemical group 0.000 description 6
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical class O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 6
- JYSUYJCLUODSLN-UHFFFAOYSA-N 1,3-benzothiazol-2-ylhydrazine Chemical compound C1=CC=C2SC(NN)=NC2=C1 JYSUYJCLUODSLN-UHFFFAOYSA-N 0.000 description 4
- KHPWPRCEHZFRKP-UHFFFAOYSA-N 2-amino-4H-pyrazol-3-one Chemical compound NN1N=CCC1=O KHPWPRCEHZFRKP-UHFFFAOYSA-N 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 235000019441 ethanol Nutrition 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- SCZGZDLUGUYLRV-UHFFFAOYSA-N (2-methylphenyl)hydrazine Chemical compound CC1=CC=CC=C1NN SCZGZDLUGUYLRV-UHFFFAOYSA-N 0.000 description 2
- ICKZKXLORXDTGV-UHFFFAOYSA-N 1-phenoxy-1-phenylhydrazine Chemical compound C=1C=CC=CC=1N(N)OC1=CC=CC=C1 ICKZKXLORXDTGV-UHFFFAOYSA-N 0.000 description 2
- WETWJCDKMRHUPV-UHFFFAOYSA-N Acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 2
- 240000000800 Allium ursinum Species 0.000 description 2
- PASDCCFISLVPSO-UHFFFAOYSA-N Benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 2
- LGROKZMEHJZWDU-UHFFFAOYSA-N N-amino-N-phenylnitramide Chemical compound [O-][N+](=O)N(N)C1=CC=CC=C1 LGROKZMEHJZWDU-UHFFFAOYSA-N 0.000 description 2
- 239000012346 acetyl chloride Substances 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 125000001769 aryl amino group Chemical group 0.000 description 2
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- WHRIKZCFRVTHJH-UHFFFAOYSA-N ethylhydrazine Chemical compound CCNN WHRIKZCFRVTHJH-UHFFFAOYSA-N 0.000 description 2
- 125000001841 imino group Chemical group [H]N=* 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- XBCIOBSQHJYVBQ-UHFFFAOYSA-N naphthalen-1-ylhydrazine Chemical compound C1=CC=C2C(NN)=CC=CC2=C1 XBCIOBSQHJYVBQ-UHFFFAOYSA-N 0.000 description 2
- 235000020004 porter Nutrition 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- NWELCUKYUCBVKK-UHFFFAOYSA-N pyridin-2-ylhydrazine Chemical compound NNC1=CC=CC=N1 NWELCUKYUCBVKK-UHFFFAOYSA-N 0.000 description 2
- QMVCLSHKMIGEFN-UHFFFAOYSA-N quinolin-2-ylhydrazine Chemical compound C1=CC=CC2=NC(NN)=CC=C21 QMVCLSHKMIGEFN-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 230000002194 synthesizing Effects 0.000 description 2
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/18—One oxygen or sulfur atom
- C07D231/20—One oxygen atom attached in position 3 or 5
- C07D231/22—One oxygen atom attached in position 3 or 5 with aryl radicals attached to ring nitrogen atoms
Definitions
- hydrazine are valuable couplers for color photography and the lack of suitability of the Conradlz Zart method for their preparation necessitated a search for other methods.
- an object of the present invention to provide a new method for the preparation of aminopyrazolones.
- a further object is to provide a less drastic treatment of aryl, hy-.
- R ary l, alkyl, or a heterocyclicgroup.
- heterocyclic hydrazlne's e. g., z-benzo min hydrazine, 2-pyridyl hydrazine and 2- quinolyl hydrazine and cyanacetic eater
- the 3- hydroxy-5-pyrazolone imides are obtained while the new method gives the 3-amino-5 -pyrazo- Ethyl (p-ethoxy-p-imlno)propionate is described in the literature as the imino.
- ethyl ether of ethyl cyanoacetate Berichte, vol. 28, page 478, 1895.
- Our new synthesis is carried out by merely heating the two reactants on the steam both with or without a solvent.
- Our method may be used with hydrazine itself, aryl hydrazlnes such as phenyl hydrazine, tolyl hydrazine, phenoxyphenyl hydrazine, nitrophenyl hydrazine, naphthyl hydrazine, and others, as well as with alkyl hydrazines, such as methyl and ethyl hydrazine, and heterocyclicsubstituted hydrazines.
- aryl hydrazlnes such as phenyl hydrazine, tolyl hydrazine, phenoxyphenyl hydrazine, nitrophenyl hydrazine, naphthyl hydrazine, and others
- alkyl hydrazines such as methyl and ethyl hydrazine
- heterocyclicsubstituted hydrazines such as methyl and ethyl hydrazine
- Example 1 N GNH: I-phenyI S-amInoJ-pyrazoIoneQN
- a mixture of 10 grams (.063 mole) of ethyl (pethoxy-p-imino) propionate and 6.8 grams (.063 mole) of phenyl hydrazine was heated on the steam bath for three hours.
- the resulting mush was slurried with 20 cc. of methyl alcohol, cooled and filtered.
- the yield was 5.5 grams '(50%),
- Example 3 1 (2'-benzothiazolyl) -3-amino-5-pyrazoione (a) Ethyl-p[p'(2 benzothiazolyl)hydrazine]- p-imino-propionate.
- the compounds produced by our method may be acylated in the usual way to produce acyl derivatives useful in color photography.
- Treatment of the aryl amino pyrazolone with acetyl chloride or benzoyl chloride produces a. monoacetyl or monobenzoyl derivative soluble in alkali which functions as a coupler.
- a pyrazolone derivative which comprises condensing a hydrazine selected from the class consisting of alkyl hydrazines, aryl hydrazines, and heterocyclic hydrazines, with ethyl (p-ethoxy-p-imino)propionate.
- R is selected from the class consisting of alkyl groups, aryl groups, and heterocyclic groups, which comprises condensing a hydrazine selected from the class consisting of alkyl hydrazines, aryi hydrazines, and heterocycllc hydrazines, with ethyKp-ethOXy-p-iminQ) propionate.
- R is an aryl group, which comprises condensing an aryl hydrazine with ethylQB-ethoxyfl-imino) propionate.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
Description
Patented May 22, 194,5
UNITED STATES PATENT orncs PREPARATION OF AMINO PYBAZOLONES Henry 1). Porter and Arnold Weissberger, Rochester, N. Y., asslgnors to Eastman Kodak Company, RochestenN. Y., .a corporation of New Jersey No Drawing. Application November 5, 194 2,
1 Serial No. 464,650
I Claims. (Cl. 260-305) This invention relates to the preparation of amino pyrazolones.
The preparation of 1-phenyl-3-hydroxy-5-pyrazolone imide is described by Conrad is Zart in Berlchte, vol. 39 (1906), page 2287. The reaction involves the use of phenyl hydrazine and ethyl cyanoacetate in the presence of sodium ethylate. These intermediates are heated for 20 hours at 120-130 -C. according t3 the Conrad .8; Zart method.
We have found that the Conrad 81 Zart method does not give 1-phenyl-3-hydroxy-6-pyrazolone imide, but produces 1-phenyl-3-amino-5-D71'azolone (J. Am. Chem. Soc., vol. 64, page 2133 (1942)). This compound, and its derivatives, are
valuable couplers for use in the color-forming process of color photography.
It is frequently desirable to prepare amino pyrazolones from hydrazines bearing substituents which will not withstand the long and drastic heat treatment demanded by the Conrad & Zart method, for example, p-nitrophenylhydrazine.
Amino pyrazolones formed from p-nitrophenyh,
hydrazine are valuable couplers for color photography and the lack of suitability of the Conradlz Zart method for their preparation necessitated a search for other methods.
It is, therefore, an object of the present invention to provide a new method for the preparation of aminopyrazolones. A further object is to provide a less drastic treatment of aryl, hy-.
drazines than that of Conrad & Zart in the preparation of amino pyrazolones. Other objects will appear frm..the rollowing description of our invention.
These objects are accomplished by condensing the appropriate phenyl hydrazine with ethyl (pethoxy-B-imlnmpropionate. v
The compounds which we produce with our new method are not all new, but the novelty resides in the provision of an easy method for preparing them. These compounds'have the following probable formula:
where R=ary l, alkyl, or a heterocyclicgroup. with heterocyclic hydrazlne's, e. g., z-benzo min hydrazine, 2-pyridyl hydrazine and 2- quinolyl hydrazine and cyanacetic eater, the 3- hydroxy-5-pyrazolone imides are obtained while the new method gives the 3-amino-5 -pyrazo- Ethyl (p-ethoxy-p-imlno)propionate is described in the literature as the imino. ethyl ether of ethyl cyanoacetate (Berichte, vol. 28, page 478, 1895). Our new synthesis is carried out by merely heating the two reactants on the steam both with or without a solvent.
Our method may be used with hydrazine itself, aryl hydrazlnes such as phenyl hydrazine, tolyl hydrazine, phenoxyphenyl hydrazine, nitrophenyl hydrazine, naphthyl hydrazine, and others, as well as with alkyl hydrazines, such as methyl and ethyl hydrazine, and heterocyclicsubstituted hydrazines.
Our invention will now be described by reference to the following specific examples:
Example 1 N=GNH: I-phenyI S-amInoJ-pyrazoIoneQN A mixture of 10 grams (.063 mole) of ethyl (pethoxy-p-imino) propionate and 6.8 grams (.063 mole) of phenyl hydrazine was heated on the steam bath for three hours. The resulting mush was slurried with 20 cc. of methyl alcohol, cooled and filtered. The yield was 5.5 grams '(50%),
M. P. 215-216 C.
' Example 2 v N=C-N Hs l-p-nitrophenyl-3-amino-5-pyrazoloneN0| ON A mixture of so-grams (.315 mole) of ethyl (nethoxy-p-imino) propionate and 48 grams (.315
mole) of p-nitrophenylhydrazine was heated together in 50 cc. of pyridine on .the steam bath for two hours. Then 50 cc. of methyl alcohol was added and the mixture cooled, 'flltered, and washed with methyl alcohol. The yield was 25 rams (36%) M. P. 248-2501 0.
Example 3 1 (2'-benzothiazolyl) -3-amino-5-pyrazoione (a) Ethyl-p[p'(2 benzothiazolyl)hydrazine]- p-imino-propionate.
A mixture of 15.9 grams (0.1 mole) of the imino ethyl ether of ethyl cyanoacetate and 16.5 grams (0.1 mole) of 2-benzothiazolylhydrazine in 75 cc.
of pyridine was heated on the steam bath for one hour. About 50 cc. of ethyl alcohol was then added and the precipitate filtered oif. Further precipitation occurred on adding water to the flitrate. A yield of 21.3 grams (76%) was obtained, M. P. 179-181" C.
(b) A solution of sodium ethylate was prepared from 4.6 grams (0.2 mole) of sodium and 100 cc. of ethyl alcohol. To this was added 27.8 grams (0.1 mole) of ethyl-p [p'(2-benzothiazoly1) hydrazinoJ-p-iminopropionate. This mixture was refluxed for one hour after which water was added to form a clear solution. Upon making acid, a heavy precipitate formed. A yield of 22.3 grams (96%) was obtained, M. P. 252-4 C.
The compounds produced by our method may be acylated in the usual way to produce acyl derivatives useful in color photography. Treatment of the aryl amino pyrazolone with acetyl chloride or benzoyl chloride produces a. monoacetyl or monobenzoyl derivative soluble in alkali which functions as a coupler.
We claim:
1. The method of producing a pyrazolone derivative, which comprises condensing a hydrazine selected from the class consisting of alkyl hydrazines, aryl hydrazines, and heterocyclic hydrazines, with ethyl (p-ethoxy-p-imino)propionate.
2. The method of producing a pyrazolone derivative of the following probable composition:
N=c-NH,
asraaeo where R is selected from the class consisting of alkyl groups, aryl groups, and heterocyclic groups, which comprises condensing a hydrazine selected from the class consisting of alkyl hydrazines, aryi hydrazines, and heterocycllc hydrazines, with ethyKp-ethOXy-p-iminQ) propionate.
' 3. The method of producing a pyrazolone derivative of the following probable composition:
where R is an aryl group, which comprises condensing an aryl hydrazine with ethylQB-ethoxyfl-imino) propionate.
4. The method of producing a 1-aryl-3-aminofi-pyrazolone, which comprises condensing an aryl hydrazine with ethyKp-ethoxy-g-imino)propionate by heating the reactants on a steam bath for two to three hours, and separating the resulting product.
5. The method of producing 1 --pheny1- 3 amino-5-pyrazolone, which comprises condenss phenyl hydrazine with ethyKp-ethOXy-p-imino)propionate by heating the reactantson a steam bath for two to three hours, and separating the resulting product.
6. The method of producing l-p-nitrophenyl- 3-amino-5-pyrazolone which comprises condensing p-nitrophenyl hydrazine with ethyl (fl-ethoxy- ,e-imino) propionate by heating the reactants on a steam bath for two or three hours, and separat ing the resulting product.
7. The method of producing 1(2'-benzothiazolyl) 3 amino-5-pyrazolone which comprises condensing 2-benzothiazolyl hydrazine with ethy1(p-ethoxy-p-imino)propionate by heating the reactants on a steam bath for about one hour in the presence of pyridine, separating the product, refluxing it with sodium ethylate, acidifying the solution, and separating the resulting product.
- HENRY D. PORTER.
ARNOLD WEISSBERGER.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2376380A true US2376380A (en) | 1945-05-22 |
Family
ID=3434606
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US2376380D Expired - Lifetime US2376380A (en) | Preparation of amino pyrazolones |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2376380A (en) |
Cited By (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2619419A (en) * | 1947-12-24 | 1952-11-25 | Gevaert Photo Prod Nv | Production of color photographic images |
| US2691659A (en) * | 1954-10-12 | Process for preparation of | ||
| US2710871A (en) * | 1951-12-05 | 1955-06-14 | Eastman Kodak Co | Preparation of 5-pyrazolone diamides |
| US2726248A (en) * | 1950-04-06 | 1955-12-06 | Ilfrod Ltd | 3-amino pyrazolines and process |
| US3065238A (en) * | 1958-03-20 | 1962-11-20 | Basf Ag | Production of 1, 3, 4-oxdiazoles |
| US3254108A (en) * | 1963-02-18 | 1966-05-31 | Eastman Kodak Co | Process for preparation of arylimino propionates |
| US3952008A (en) * | 1973-04-17 | 1976-04-20 | Bayer Aktiengesellschaft | Pyrazol-5-ones |
| US3956311A (en) * | 1970-08-29 | 1976-05-11 | Agfa-Gevaert, A.G. | Process for the preparation of 3-anilino-pyrazolones-(5) |
| US3957814A (en) * | 1973-04-17 | 1976-05-18 | Bayer Aktiengesellschaft | Pyrazol-5-ones |
| US3992404A (en) * | 1973-04-17 | 1976-11-16 | Bayer Aktiengesellschaft | Pyrazol-5-ones |
| US4000294A (en) * | 1973-04-17 | 1976-12-28 | Bayer Aktiengesellschaft | Pyrazol-5-ones |
| US4002641A (en) * | 1973-12-20 | 1977-01-11 | Bayer Aktiengesellschaft | Pyrazole derivatives |
| US4005215A (en) * | 1973-04-17 | 1977-01-25 | Bayer Aktiengesellschaft | Pyrazol-5-ones |
| US4032646A (en) * | 1973-04-17 | 1977-06-28 | Bayer Aktiengesellschaft | Pyrazol-5-ones |
| US4045571A (en) * | 1973-04-17 | 1977-08-30 | Bayer Aktiengesellschaft | Pyrazol-5-ones |
| US4053621A (en) * | 1974-06-06 | 1977-10-11 | Bayer Aktiengesellschaft | 1-[2-(βNaphthyloxy)ethyl]-3-methylpyrazolone-(5) and antithrombotic and antithrombolytic compositions and methods utilizing them |
| US4056533A (en) * | 1973-04-17 | 1977-11-01 | Bayer Aktiengesellschaft | Pyrazol-5-ones |
| US4061653A (en) * | 1972-06-23 | 1977-12-06 | Bayer Aktiengesellschaft | 1-Substituted-3-amino-pyrazol-5-ones |
| US4069334A (en) * | 1973-12-20 | 1978-01-17 | Bayer Aktiengesellschaft | Pyrazole derivatives |
| US4081596A (en) * | 1973-04-17 | 1978-03-28 | Bayer Aktiengesellschaft | Pyrazol-5-ones |
| USRE30420E (en) * | 1973-04-17 | 1980-10-21 | Bayer Aktiengesellschaft | Pyrazol-5-ones |
| US4288446A (en) * | 1973-04-17 | 1981-09-08 | Bayer Aktiengesellschaft | Pyrazol-5-ones |
| US5270156A (en) * | 1991-10-11 | 1993-12-14 | Konica Corporation | Silver halide color photographic light sensitive material |
| US5500439A (en) * | 1993-12-09 | 1996-03-19 | Alteon Inc. | Aminopyrazoles |
| EP0782044A1 (en) | 1995-12-27 | 1997-07-02 | Konica Corporation | Silver halide light-sensitive color photographic material |
-
0
- US US2376380D patent/US2376380A/en not_active Expired - Lifetime
Cited By (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2691659A (en) * | 1954-10-12 | Process for preparation of | ||
| US2619419A (en) * | 1947-12-24 | 1952-11-25 | Gevaert Photo Prod Nv | Production of color photographic images |
| US2726248A (en) * | 1950-04-06 | 1955-12-06 | Ilfrod Ltd | 3-amino pyrazolines and process |
| US2710871A (en) * | 1951-12-05 | 1955-06-14 | Eastman Kodak Co | Preparation of 5-pyrazolone diamides |
| US3065238A (en) * | 1958-03-20 | 1962-11-20 | Basf Ag | Production of 1, 3, 4-oxdiazoles |
| US3254108A (en) * | 1963-02-18 | 1966-05-31 | Eastman Kodak Co | Process for preparation of arylimino propionates |
| US3956311A (en) * | 1970-08-29 | 1976-05-11 | Agfa-Gevaert, A.G. | Process for the preparation of 3-anilino-pyrazolones-(5) |
| US4061653A (en) * | 1972-06-23 | 1977-12-06 | Bayer Aktiengesellschaft | 1-Substituted-3-amino-pyrazol-5-ones |
| US4005215A (en) * | 1973-04-17 | 1977-01-25 | Bayer Aktiengesellschaft | Pyrazol-5-ones |
| US3952008A (en) * | 1973-04-17 | 1976-04-20 | Bayer Aktiengesellschaft | Pyrazol-5-ones |
| US4000294A (en) * | 1973-04-17 | 1976-12-28 | Bayer Aktiengesellschaft | Pyrazol-5-ones |
| US4288446A (en) * | 1973-04-17 | 1981-09-08 | Bayer Aktiengesellschaft | Pyrazol-5-ones |
| US3957814A (en) * | 1973-04-17 | 1976-05-18 | Bayer Aktiengesellschaft | Pyrazol-5-ones |
| US4032646A (en) * | 1973-04-17 | 1977-06-28 | Bayer Aktiengesellschaft | Pyrazol-5-ones |
| US4045571A (en) * | 1973-04-17 | 1977-08-30 | Bayer Aktiengesellschaft | Pyrazol-5-ones |
| USRE30420E (en) * | 1973-04-17 | 1980-10-21 | Bayer Aktiengesellschaft | Pyrazol-5-ones |
| US4056533A (en) * | 1973-04-17 | 1977-11-01 | Bayer Aktiengesellschaft | Pyrazol-5-ones |
| US3992404A (en) * | 1973-04-17 | 1976-11-16 | Bayer Aktiengesellschaft | Pyrazol-5-ones |
| US4081596A (en) * | 1973-04-17 | 1978-03-28 | Bayer Aktiengesellschaft | Pyrazol-5-ones |
| US4069334A (en) * | 1973-12-20 | 1978-01-17 | Bayer Aktiengesellschaft | Pyrazole derivatives |
| US4002641A (en) * | 1973-12-20 | 1977-01-11 | Bayer Aktiengesellschaft | Pyrazole derivatives |
| US4053621A (en) * | 1974-06-06 | 1977-10-11 | Bayer Aktiengesellschaft | 1-[2-(βNaphthyloxy)ethyl]-3-methylpyrazolone-(5) and antithrombotic and antithrombolytic compositions and methods utilizing them |
| US5270156A (en) * | 1991-10-11 | 1993-12-14 | Konica Corporation | Silver halide color photographic light sensitive material |
| US5500439A (en) * | 1993-12-09 | 1996-03-19 | Alteon Inc. | Aminopyrazoles |
| EP0782044A1 (en) | 1995-12-27 | 1997-07-02 | Konica Corporation | Silver halide light-sensitive color photographic material |
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