GB737105A - Improvements in and relating to pyrazolone derivatives and their use as colour couplers in colour photographic development - Google Patents

Improvements in and relating to pyrazolone derivatives and their use as colour couplers in colour photographic development

Info

Publication number
GB737105A
GB737105A GB30735/52A GB3073552A GB737105A GB 737105 A GB737105 A GB 737105A GB 30735/52 A GB30735/52 A GB 30735/52A GB 3073552 A GB3073552 A GB 3073552A GB 737105 A GB737105 A GB 737105A
Authority
GB
United Kingdom
Prior art keywords
pyrazolone
tert
amylphenoxy
prepared
amino
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
Application number
GB30735/52A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Kodak Ltd
Original Assignee
Kodak Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Kodak Ltd filed Critical Kodak Ltd
Publication of GB737105A publication Critical patent/GB737105A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • G03C7/36—Couplers containing compounds with active methylene groups
    • G03C7/38—Couplers containing compounds with active methylene groups in rings
    • G03C7/384—Couplers containing compounds with active methylene groups in rings in pyrazolone rings
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

A pyrazolone derivative of the general formula <FORM:0737105/IV (b)/1> wherein D represents a p-arylene group of the benzene series, X represents an aryl group of the benzene series and Z represents an alkyl group or an aralkyl or aryl group of the benzene series, are prepared by acylating a 1-nitroaryl-3-amino-5-pyrazolone, reducing the nitro group, and acylating the resulting amino group. Alternatively, the nitro group may first be reduced and both amino groups acylated simultaneously. 1 - {41 - [311 - (4111 - Tert. - amylphenoxybenzamido] - phenyl} - 3 - [311 - (4111 - tert. amylphenoxy) - benzamido] - 5 - pyrazolone is prepared by adding 3-(4-tert.-amylphenoxy)-benzoyl chloride to a pyridine solution of 1-p-aminophenyl - 3 - amino - 5 - pyrazolone at a controlled rate. 1 - {4 - [3 - (4 - tert. - amylphenoxy) - x - chlorosulphonyl - benzamido] - phenyl} - 3 - [3 - (4 - tert. - amylphenoxy) - x - chlorosulphonyl] - benzamido - 5 - pyrazolone is similarly prepared. 1 - {41 - [311 - (4111 - Tert. - amylphenoxy) - x - chlorosulphonyl - benzamido] - phenyl} - 3 - (2 : 4 - di - tert. - amylphenoxy) - acetamido - 5 - pyrazolone is prepared by treating a dioxane solution of 1 - (4 - aminophenyl) - 3 - (2 : 4 - di - tert. - amylphenoxy) - acetamido - 5 - pyrazolone with a dioxane solution of 3-(4-tert.-amylphenoxy)-x-chlorosulphonyl-benzoyl chloride and then adding quinoline. 1 - [4 - (3 - Chlorosulphonylbenzamido) - phenyl] - 3 - lauramido - 5 - pyrazolone, 1 - [41 - (211 - sulphobenzamido) - phenyl] - 3 - stearamido - 5 - pyrazolone, 1 - [4 - (3 - chlorosulphonylbenzamido) - phenyl] - 3 - stearamido - 5 - pyrazolone, 1 - [4 - (3 - sulphobenzamido) - phenyl] - 3 - [g - (2 : 4 - di - tert. - amylphenoxy) - butyramido] - 5 - pyrazolone, and 1 - [4 - (3 - sulphobenzamido) - phenyl] - 3 - (2 : 4 - di - tert. - amylphenoxy) - acetamido - 5 - pyrazolone are similarly prepared. 1 - p - Aminophenyl - 3 - amino - 5 - pyrazolone is prepared by reducing 1-p-nitrophenyl-3-amino-5-pyrazolone suspended in water with hydrogen in the presence of Raney nickel. 1 - p - Nitrophenyl - 3 - amino - 5 - pyrazolone is prepared by heating together ethyl (b -ethoxy : b -imino)-propionate and p-nitrophenylhydrazine in pyridine. 1 - (4 - Nitrophenyl) - 3 - (2 : 4 - di - tert. - amylphenoxy) - acetamido - 5 - pyrazolone is prepared by acylating 1 - (p - nitrophenyl) - 3 - amino - 5-pyrazolone with 2 : 4-di-tert.-amylphenoxyacetyl chloride in dry dioxane. 1 - (4 - Aminophenyl) - 3 - (2 : 4 - di - tert. - amylphenoxy) - acetamido - 5 - pyrazolone is prepared by reducing 1-(4-nitrophenyl)-3-(2 : 4-di-tert. - amylphenoxy) - acetamido - 5 - pyrazolone with hydrogen in benzene in the presence of Raney nickel. 1 - (4 - Nitrophenyl) - 3 - lauramido - 5 - pyrazolone is prepared by reacting 1-(4-nitrophenyl) - 3 - amino - 5 - pyrazolone with lauroyl chloride in pyridine, and 1-(4-aminophenyl)-3-lauramido-5-pyrazolone by reduction as above 1 - (4 - Nitrophenyl) - 3 - stearamido - 5 - pyrazolone and 1 - (4 - aminophenyl) - 3 - stearamido - 5-pyrazolone are similarly prepared. 3 - (4 - Tert. - amylphenoxy) - x - chlorosulphonyl benzoyl chloride is prepared by refluxing together x-chlorosulphonyl-4-tert.-amylphenoxy-3-benzoic acid and phosphorus pentachloride. X - Chlorosulphonyl - 4 - tert. - amylphenoxy - 3 - benzoic acid is prepared by adding 41-tert.-amylphenoxy-3-benzoic acid in small portions to cooled chlorosulphonic acid. 41 - Tert. - amylphenoxy - 3 - benzoic acid is prepared by heating together m-bromobenzoic acid, p-tert.-amylphenol, sodium hydroxide, and copper bronze powder. Specifications 541,589, [Group XX], and 737,103 are referred to.
GB30735/52A 1951-12-05 1952-12-04 Improvements in and relating to pyrazolone derivatives and their use as colour couplers in colour photographic development Expired GB737105A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US260097A US2710871A (en) 1951-12-05 1951-12-05 Preparation of 5-pyrazolone diamides

Publications (1)

Publication Number Publication Date
GB737105A true GB737105A (en) 1955-09-21

Family

ID=22987749

Family Applications (1)

Application Number Title Priority Date Filing Date
GB30735/52A Expired GB737105A (en) 1951-12-05 1952-12-04 Improvements in and relating to pyrazolone derivatives and their use as colour couplers in colour photographic development

Country Status (3)

Country Link
US (1) US2710871A (en)
FR (1) FR1077534A (en)
GB (1) GB737105A (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3087933A (en) * 1963-04-30 -nhxso
US8686048B2 (en) * 2010-05-06 2014-04-01 Rhizen Pharmaceuticals Sa Immunomodulator and anti-inflammatory compounds

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2068790A (en) * 1937-01-26 Pyrazolones containing wholly or
US2376380A (en) * 1945-05-22 Preparation of amino pyrazolones
US1841621A (en) * 1926-05-12 1932-01-19 British Dyestuffs Corp Ltd Manufacture of pyrazolone compounds
BE443050A (en) * 1940-10-19
US2343703A (en) * 1942-09-04 1944-03-07 Eastman Kodak Co Pyrazolone coupler for color photography

Also Published As

Publication number Publication date
FR1077534A (en) 1954-11-09
US2710871A (en) 1955-06-14

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