GB599919A - Improvements in the manufacture of aminopyrazolones and their use as colour couplers - Google Patents
Improvements in the manufacture of aminopyrazolones and their use as colour couplersInfo
- Publication number
- GB599919A GB599919A GB2475144A GB2475144A GB599919A GB 599919 A GB599919 A GB 599919A GB 2475144 A GB2475144 A GB 2475144A GB 2475144 A GB2475144 A GB 2475144A GB 599919 A GB599919 A GB 599919A
- Authority
- GB
- United Kingdom
- Prior art keywords
- pyrazolone
- amino
- group
- quinolyl
- ethyl
- 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
Links
- XSFKCGABINPZRK-UHFFFAOYSA-N 4-aminopyrazol-3-one Chemical class NC1=CN=NC1=O XSFKCGABINPZRK-UHFFFAOYSA-N 0.000 title 1
- 238000004519 manufacturing process Methods 0.000 title 1
- -1 imino ethyl Chemical group 0.000 abstract 4
- XNINAOUGJUYOQX-UHFFFAOYSA-M 2-cyanobutanoate Chemical compound CCC(C#N)C([O-])=O XNINAOUGJUYOQX-UHFFFAOYSA-M 0.000 abstract 2
- XGKOIOPVLYCTRF-UHFFFAOYSA-N 5-amino-2-methyl-4H-pyrazol-3-one Chemical compound CN1N=C(N)CC1=O XGKOIOPVLYCTRF-UHFFFAOYSA-N 0.000 abstract 2
- 230000000875 corresponding Effects 0.000 abstract 2
- 230000001808 coupling Effects 0.000 abstract 2
- 238000010168 coupling process Methods 0.000 abstract 2
- 238000005859 coupling reaction Methods 0.000 abstract 2
- 239000000975 dye Substances 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- ZIUSEGSNTOUIPT-UHFFFAOYSA-N ethyl 2-cyanoacetate Chemical compound CCOC(=O)CC#N ZIUSEGSNTOUIPT-UHFFFAOYSA-N 0.000 abstract 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 2
- 238000010438 heat treatment Methods 0.000 abstract 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 abstract 2
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical class O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 abstract 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 abstract 2
- QITJGSMHKVXOFR-UHFFFAOYSA-N 1,3-benzoxazol-2-ylhydrazine Chemical compound C1=CC=C2OC(NN)=NC2=C1 QITJGSMHKVXOFR-UHFFFAOYSA-N 0.000 abstract 1
- IOEQZAIBXFYINW-UHFFFAOYSA-N 2-pentoxyaniline Chemical compound CCCCCOC1=CC=CC=C1N IOEQZAIBXFYINW-UHFFFAOYSA-N 0.000 abstract 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 abstract 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 abstract 1
- PASDCCFISLVPSO-UHFFFAOYSA-N Benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 abstract 1
- HDZGCSFEDULWCS-UHFFFAOYSA-N Monomethylhydrazine Chemical compound CNN HDZGCSFEDULWCS-UHFFFAOYSA-N 0.000 abstract 1
- ODUCDPQEXGNKDN-UHFFFAOYSA-N Nitroxyl Chemical class O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 abstract 1
- BHAAPTBBJKJZER-UHFFFAOYSA-N P-Anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 abstract 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N Sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 abstract 1
- 150000001263 acyl chlorides Chemical class 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 125000004423 acyloxy group Chemical group 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 abstract 1
- 150000008049 diazo compounds Chemical class 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 229940083761 high-ceiling diuretics Pyrazolone derivatives Drugs 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 230000003301 hydrolyzing Effects 0.000 abstract 1
- 238000002955 isolation Methods 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 abstract 1
- RCIGDGBXEMECGY-UHFFFAOYSA-N pyridin-3-ylhydrazine Chemical compound NNC1=CC=CN=C1 RCIGDGBXEMECGY-UHFFFAOYSA-N 0.000 abstract 1
- KRTLKPFLTASKCG-UHFFFAOYSA-N pyridin-4-ylhydrazine Chemical compound NNC1=CC=NC=C1 KRTLKPFLTASKCG-UHFFFAOYSA-N 0.000 abstract 1
- IISWOHCLTBUICM-UHFFFAOYSA-N quinolin-3-ylhydrazine Chemical compound C1=CC=CC2=CC(NN)=CN=C21 IISWOHCLTBUICM-UHFFFAOYSA-N 0.000 abstract 1
- 238000010792 warming Methods 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom 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
- C07D231/44—Oxygen and nitrogen or sulfur and nitrogen atoms
- C07D231/52—Oxygen atom in position 3 and nitrogen atom in position 5, or vice versa
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
Abstract
Pyrazolone derivatives of the probable general formula <FORM:0599919/IV/1> wherein R represents an alkyl or heterocyclic radical and R1 hydrogen or an acyl group, are manufactured by heating together, if necessary in the presence of alkali (e.g. sodium methylate or ethylate), an alkylhydrazine or a heterocyclic hydrazine and a b -alkoxy-b -iminopropionic ester (i.e. the iminoether derivative of a cyanoacetic ester), or by heating together a 3- or a 4-pyridylhydrazine and a cyanoacetic ester, and in either case, if desired, acylating the product by warming it with two molecular proportions of an acyl chloride to form an acylamino-acyloxy-pyrazole and then hydrolysing the acyloxy group by adding water to a warm solution of the pyrazole in an organic solvent. The products may be employed as colour couplers in colour photographic development (see Group XX). In examples, the imino ethyl ether of ethyl cyanoacetate is condensed with 2-benzthiazolyl-, 2-, 3- and 4-pyridyl-, 2-quinolyl- and 2-benzoxazolyl-hydrazine to produce the corresponding 1-substituted 3-amino-5-pyrazolones, in some cases with intermediate isolation of the corresponding b -(substituted-hydrazino)-b -iminopropionic ester. In a further example, 1-(21-quinolyl)-3-amino-5-pyrazolone is acylated with 2 molecular proportions of benzoyl chloride and the product partially hydrolysed to 1 - (21 - quinolyl) - 3 - benzoylamino - 5 - pyrazolone. Specifications 427,516, 427,520, 440,032, 440,089, 447,092, [all in Group XX], 478,990, 507,841, 524,154, 524,554, 524,555, 541,589, [all in Group XX], 547,064 and 553,506 are referred to. Azo dyestuffs are manufactured by coupling a diazo compound with a pyrazolone of the general formula above. Samples have been furnished under Sect. 2 (5) of: (1) 1 - methyl - 3 - amino - 5 - pyrazolone obtained (together with the 3-hydroxy compound) from methylhydrazine and ethyl b -ethoxy-b -iminopropionate; (2) 1-(31-pyridyl)-3-amino-5-pyrazolone prepared from 3-pyridylhydrazine and ethyl cyanoacetate; (3) the dyestuff o-amyloxyaniline --> 1-(31-quinolyl)-3-[311-(2111 : 4111 - diamylphenoxyacetamido) - benz - amido]-5-pyrazolone (the coupling component being prepared from 3-quinolylhydrazine, ethyl b - ethoxy - b - iminopropionate and 3 - (21 : 41-diamylphenoxyacetamido) - benzoyl chloride); (4) the dyestuff p-anisidine --> 1-methyl-3-amino-5-pyrazolone.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB599919A true GB599919A (en) | 1948-03-24 |
Family
ID=1738624
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2475144A Expired GB599919A (en) | 1944-12-11 | Improvements in the manufacture of aminopyrazolones and their use as colour couplers |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB599919A (en) |
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2618641A (en) * | 1951-12-15 | 1952-11-18 | Eastman Kodak Co | Arylidene-bis-pyrazolones |
| US3356686A (en) * | 1960-04-13 | 1967-12-05 | Du Pont | Substituted amidopyrazalones containing a terminal ethylenically unsaturated group |
| 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 |
| 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 |
-
1944
- 1944-12-11 GB GB2475144A patent/GB599919A/en not_active Expired
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2618641A (en) * | 1951-12-15 | 1952-11-18 | Eastman Kodak Co | Arylidene-bis-pyrazolones |
| US3356686A (en) * | 1960-04-13 | 1967-12-05 | Du Pont | Substituted amidopyrazalones containing a terminal ethylenically unsaturated group |
| US4061653A (en) | 1972-06-23 | 1977-12-06 | Bayer Aktiengesellschaft | 1-Substituted-3-amino-pyrazol-5-ones |
| US4000294A (en) | 1973-04-17 | 1976-12-28 | Bayer Aktiengesellschaft | Pyrazol-5-ones |
| US4005215A (en) | 1973-04-17 | 1977-01-25 | Bayer Aktiengesellschaft | Pyrazol-5-ones |
| US4045571A (en) | 1973-04-17 | 1977-08-30 | Bayer Aktiengesellschaft | Pyrazol-5-ones |
| US4056533A (en) | 1973-04-17 | 1977-11-01 | Bayer Aktiengesellschaft | Pyrazol-5-ones |
| 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 |
| US4002641A (en) | 1973-12-20 | 1977-01-11 | Bayer Aktiengesellschaft | Pyrazole derivatives |
| US4069334A (en) | 1973-12-20 | 1978-01-17 | 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 |
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