Patent GB-825311-A (GB)
Title: Photographic silver halide emulsions and photographic developers containing colour couplers and method of producing coloured photographic images
IPC: G03C7/32
Filed: 1957-07-29
Abstract: 2 - Heptafluoro - n - butyramido - 5 - methyl phenol is prepared by reacting 2-amino-5-methyl phenol with heptafluoro-n-butyryl chloride in the presence of quinoline.  The following amines are similarly reacted with heptafluoro-n-butyryl chloride:-6-amino-2,4-dichloro-3-methyl phenol, 2 - amino - 5 - n - pentadecyl - phenol, 2 - amino - 5 - nitro - phenol, 1 - phenyl - 3 - amino - 5-pyrazolone (in the presence of N,N-dimethylaniline instead of quinoline), 1-(4-nitrophenyl)-3-amino-5-pyrazolone (also in the presence of N,N-dimethylaniline) and 5-amino-1-naphthol.  Similarly, 2-amino-5-nitrophenol is reacted with trifluoro-acetic anhydride in the presence of quinoline to give 5-nitro-2-trifluoroacetamido-phenol.  a  - (4 - Heptafluoro - n - butyramido-benzoyl)acetanilide is prepared by reacting a -(4-aminobenzoyl)acetanilide with heptafluoro-n-butytyl chloride in the presence of sodium acetate and glacial acetic acid. Similarly, a -(4-aminobenzoyl)acetanilide is reacted with trifluoroacetic anhydride, and a -benzoyl-4-amino-acetanilide is reacted with heptafluoro-n-butyryl chloride or with trifluoroacetic anhydride.  A compound which is apparently 2-(a -heptafluoro - n - butyrylamino) - 5 - [(21,41-di-n-amyl - phenoxy) - acetylamino] - phenol is prepared by reacting 5-amino-2-heptafluoro-n-butyramidophenol with a -(2,4-di-n-amylphenoxy)acetyl chloride in the presence of quinoline. The following acid chlorides are similarly reacted with the aminophenol derivative:-a  - (2,4 - di - n (and t-) - amylphenoxy)butyryl chloride, a  - (2,4 - di - t - amylphenoxy)caproyl chloride, a -(2,4-di-t-amylphenoxy)heptoyl chloride, a  - (2,4 - di - t - amylphenoxy)caprylyl-chloride, a  - (3 - n - pentadecylphenoxy)butyryl chloride, g  - (2,4 - di - n (and t-) - amylphenoxy)-butyryl chloride and g -(4-n-amyl-2-n-nonylphenoxy)butyryl chloride.  Similarly, 5-amino-2-trifluoroacetamido phenol is reacted with g -(2,4-di-t-amylphenoxy)butyryl chloride and 1 - (4 - aminophenyl) - 3 - heptafluoro - n - butyramido-5-pyrazolone is reacted with a -(2,4-di-t-amylphenoxy)butyry chloride.  5 - Amino - 2 - heptafluoro - n - butyramido phenol is prepared by reducing the 5-nitro compound with hydrogen under pressure, using a nickel catalyst.  The following nitro compounds are similarly reduced to the amino derivatives:-5-nitro-2-trifluoroacetamido phenol and 1 - (4 - nitrophenyl) - 3 - heptafluoro - n-butyramido-5-pyrazolone.  a  - (2,4 - Di - t - amylphenoxy)caproic acid is prepared by adding ethyl a -bromocaproate to 2,4 - di - t - amylphenol in the presence of sodium methoxide.  The reaction mixture is heated with sodium hydroxide, and poured into dilute hydrochloric acid.  The caproic acid chloride is made by refluxing the acid with thionyl chloride. Similarly, acids and acid chlorides are prepared using 2,4-di-t-amylphenol and ethyl a -bromoheptoate or ethyl a -bromocaprylate.  Specifications 524,154, 524,554, 524,555, 536,577, 541,589, [all in Group XX], 649,660, 797,141 and U.S.A. Specification 2,376,380 are referred to.