GB1005238A - New pyrazolone compounds and processes for their preparation - Google Patents
New pyrazolone compounds and processes for their preparationInfo
- Publication number
- GB1005238A GB1005238A GB4478064A GB4478064A GB1005238A GB 1005238 A GB1005238 A GB 1005238A GB 4478064 A GB4478064 A GB 4478064A GB 4478064 A GB4478064 A GB 4478064A GB 1005238 A GB1005238 A GB 1005238A
- Authority
- GB
- United Kingdom
- Prior art keywords
- radical
- phenyl
- preparation
- carboethoxy
- 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
Links
- 238000002360 preparation method Methods 0.000 title abstract 3
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical class O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 title abstract 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- 229940051880 analgesics and antipyretics pyrazolones Drugs 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- ULSWTWZSRIQKBI-UHFFFAOYSA-N [4-acetyloxy-3-(2-anilinoethyl)phenyl] acetate Chemical compound C(C)(=O)OC1=C(CCNC2=CC=CC=C2)C=C(C=C1)OC(C)=O ULSWTWZSRIQKBI-UHFFFAOYSA-N 0.000 abstract 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 abstract 1
- 125000004423 acyloxy group Chemical group 0.000 abstract 1
- 239000007864 aqueous solution Substances 0.000 abstract 1
- 150000008049 diazo compounds Chemical class 0.000 abstract 1
- 150000001989 diazonium salts Chemical class 0.000 abstract 1
- DVSDDICSXBCMQJ-UHFFFAOYSA-N diethyl 2-acetylbutanedioate Chemical compound CCOC(=O)CC(C(C)=O)C(=O)OCC DVSDDICSXBCMQJ-UHFFFAOYSA-N 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- 239000000243 solution Substances 0.000 abstract 1
- 238000003756 stirring Methods 0.000 abstract 1
- 150000003900 succinic acid esters Chemical class 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B43/00—Preparation of azo dyes from other azo compounds
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B39/00—Other azo dyes prepared by diazotising and coupling
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
- G03C7/00—Multicolour photographic processes or agents therefor; Regeneration of such processing agents; Photosensitive materials for multicolour processes
- G03C7/30—Colour processes using colour-coupling substances; Materials therefor; Preparing or processing such materials
- G03C7/32—Colour coupling substances
- G03C7/333—Coloured coupling substances, e.g. for the correction of the coloured image
- G03C7/3335—Coloured coupling substances, e.g. for the correction of the coloured image containing an azo chromophore
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
- G03C8/00—Diffusion transfer processes or agents therefor; Photosensitive materials for such processes
- G03C8/02—Photosensitive materials characterised by the image-forming section
- G03C8/08—Photosensitive materials characterised by the image-forming section the substances transferred by diffusion consisting of organic compounds
- G03C8/10—Photosensitive materials characterised by the image-forming section the substances transferred by diffusion consisting of organic compounds of dyes or their precursors
- G03C8/12—Photosensitive materials characterised by the image-forming section the substances transferred by diffusion consisting of organic compounds of dyes or their precursors characterised by the releasing mechanism
- G03C8/14—Oxidation of the chromogenic substances
- G03C8/16—Oxidation of the chromogenic substances initially diffusible in alkaline environment
- G03C8/18—Dye developers
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
- Heat Sensitive Colour Forming Recording (AREA)
- Coloring (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
The invention comprises pyrazolones of formula <FORM:1005238/C2/1> wherein Z is an alkyl radical, Ar is a phenyl radical, M is an alkylene radical, n is 0 or 1 and Y1 is an ortho- or para-dihydroxyphenyl radical or a diacyloxy derivative thereof, preferably a diacetoxy radical. The pyrazolones are prepared by diazotizing a compound of formula Y1-(M)n-Ar-NH2 and reacting the diazo compound with a substituted succinic acid ester. The compounds obtained by hydrolysis of the acyloxy groups to yield hydroxy groups are used in the preparation of photographic dye developers. In an example, 2,5-diacetoxy-phenethylaniline is diazotized and the aqueous solution of the diazonium compound added slowly with stirring to a cooled solution of diethyl acetosuccinate in pyridine. The mixture is stirred for 20 hours, acidified with concentrated hydrochloric acid and extracted with ether to yield 1[p-(21, 51-diacetoxyphenethyl)-phenyl] - 3 - carboethoxy - 5 - pyrazolone. The preparation of 1-[p-(21, 51-diacetoxyphenylpropyl) - phenyl] - and 1 - [p - (21, 51 - diacetoxyphenyl) - phenyl] - 3 - carboethoxy - 5 - pyrazolone is also described. Specification 853,479 also is referred to.
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US13046861A | 1961-08-10 | 1961-08-10 | |
| US13048961A | 1961-08-10 | 1961-08-10 | |
| US13046761A | 1961-08-10 | 1961-08-10 | |
| US13049861A | 1961-08-10 | 1961-08-10 | |
| US209230A US3183090A (en) | 1962-07-11 | 1962-07-11 | Photographic products, processes, and compositions employing azo dye developers |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1005238A true GB1005238A (en) | 1965-09-22 |
Family
ID=27537873
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3021562A Expired GB1005237A (en) | 1961-08-10 | 1962-08-07 | Novel monoazo dye developers and their use in photographic processes and compositions |
| GB4478064A Expired GB1005238A (en) | 1961-08-10 | 1962-08-07 | New pyrazolone compounds and processes for their preparation |
| GB2734863A Expired GB1021940A (en) | 1961-08-10 | 1963-07-10 | Novel monoazo dyes and their use as photographic dye developers |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3021562A Expired GB1005237A (en) | 1961-08-10 | 1962-08-07 | Novel monoazo dye developers and their use in photographic processes and compositions |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2734863A Expired GB1021940A (en) | 1961-08-10 | 1963-07-10 | Novel monoazo dyes and their use as photographic dye developers |
Country Status (3)
| Country | Link |
|---|---|
| BE (2) | BE621310A (en) |
| DE (3) | DE1289589B (en) |
| GB (3) | GB1005237A (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5549733B2 (en) * | 1973-09-18 | 1980-12-13 | ||
| EP1392661A1 (en) * | 2001-05-16 | 2004-03-03 | Boehringer Ingelheim Pharmaceuticals Inc. | Diarylurea derivatives useful as anti-inflammatory agents |
| CA2670345A1 (en) * | 2006-12-01 | 2008-06-12 | Stategics, Inc. | Thrombopoietin mimetics |
-
0
- BE BE634840D patent/BE634840A/xx unknown
- BE BE621310D patent/BE621310A/xx unknown
-
1962
- 1962-08-07 GB GB3021562A patent/GB1005237A/en not_active Expired
- 1962-08-07 GB GB4478064A patent/GB1005238A/en not_active Expired
- 1962-08-10 DE DE1962J0022233 patent/DE1289589B/en active Pending
-
1963
- 1963-07-04 DE DE19631444704 patent/DE1444704A1/en active Pending
- 1963-07-04 DE DE19631797496 patent/DE1797496C3/en not_active Expired
- 1963-07-10 GB GB2734863A patent/GB1021940A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE1797496B2 (en) | 1973-04-19 |
| BE621310A (en) | |
| GB1005237A (en) | 1965-09-22 |
| GB1021940A (en) | 1966-03-09 |
| DE1289589B (en) | 1969-02-20 |
| DE1797496A1 (en) | 1971-11-18 |
| DE1572017A1 (en) | 1970-02-19 |
| DE1797496C3 (en) | 1973-11-08 |
| BE634840A (en) | |
| DE1444704A1 (en) | 1969-02-20 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| GB680488A (en) | Improvements in colour photographic couplers | |
| GB804975A (en) | Improvements relating to process for preparing dye developers | |
| GB956261A (en) | Pyrazolone colour couplers | |
| GB869776A (en) | Isobutyrophenone compounds and the production thereof | |
| GB1005238A (en) | New pyrazolone compounds and processes for their preparation | |
| GB599919A (en) | Improvements in the manufacture of aminopyrazolones and their use as colour couplers | |
| GB1043505A (en) | Water-soluble disazo-dyestuffs and process for preparing them | |
| GB1077194A (en) | Selective herbicidal compositions | |
| GB1481161A (en) | 5-(substituted-benzoyloxy)pyrazoles and a process for their conversion to 4-benzoyl-pyrazole derivatives | |
| GB540636A (en) | Improvements relating to coupling components for use in colour photography | |
| GB745545A (en) | Improvements in photographic colour couplers | |
| GB1059813A (en) | Novel processes for the preparation of intermediates useful in the preparation of colchicine compounds, and the intermediates thus prepared | |
| GB1076937A (en) | ª-arylsulphonylethyl thiosulphuric acids, their metal salts and process for preparing them | |
| GB537921A (en) | Coupling components for use in colour photography and the manufacture thereof and of intermediates therefor | |
| GB1018810A (en) | N-alkyl-n-acylaminoproprionamides and their use as photographic couplers | |
| GB739913A (en) | Improvements in colour photography | |
| GB737692A (en) | New colour couplers for use in colour photography | |
| GB1448948A (en) | Diffusion resistant dispersible magenta couplers in photographic silver halide materials | |
| GB823208A (en) | New herbicidal compounds | |
| GB731065A (en) | Manufacture of antidiazotates of aromatic amines containing basic substituents | |
| GB743505A (en) | Improvements in or relating to pyrazole derivatives | |
| ES266308A1 (en) | Permanent reproductions and their preparation | |
| US3256269A (en) | Mixed anhydrides of naphthylazophenyl | |
| GB774612A (en) | New trisazo dyestuffs | |
| GB753573A (en) | New dyestuffs intermediates |