Patent GB-778657-A (GB)
Title: A photographic colour developer, the production of coloured photographic images by means of colour-forming development, and coloured images so produced
IPC: C07D231/50
Filed: 1955-03-15
Abstract: 1 - Phenyl - 5 - pyrazolone - 3 - carboxylic acid hydrazide is prepared by heating together 1-phenyl - 3 - carbethoxy - 5 - pyrazolone, ethanol and hydrazine hydrate, and stirring the mixture into hydrochloric acid and ice.  1 - Phenyl - 5 - pyrazolone - 4 - amino - 3 - carboxylic acid methane sulphonhydrazide is prepared by reacting 1-phenyl-5-pyrazolone-3-carboxylic acid hydrazide with methanesulphochloride in the presence of NaOH, precipitating with HCl, forming the isonitroso derivative by reaction with acidified sodium nitrite, and reducing.  3 - Phenyl - 4 - amino - 5 - isoxazolone hydrochloride is prepared by forming the nitroso derivative of 3-phenyl-5-isoxazolone and reducing with tin sponge and hydrochloric acid.  1 - Phenyl - 4 - amino - 5 - pyrazolone - 3 - carboxylic acid amide is prepared by heating 1-phenyl - 3 - carbethoxy - 5 - pyrazolone with aqueous ammonia in an autoclave to obtain 1-phenyl - 5 - pyrazolone - 3 - carboxylic acid amide, forming the isonitroso derivative, and reducing with zinc dust and acetic acid.  1 - Phenyl - 4 - amino - 5 - pyrazolone - 3 - carboxylic acid hydrazide is prepared by forming the nitroso derivative of 1-phenyl-3-carbethoxy-5-pyrazolone, reacting with hydrazine hydrate, and reducing with tin and hydrochloric acid.  1 - (2 - Tetrahydrothiophenesulphone) - 3 - carbethoxy - 4 - amino - 5 - pyrazolone is prepared by reacting hydrazine hydrate with butadiene sulphone to obtain 2 - tetrahydrothiophenesulphonehydrazine, heating this with the sodium salt of ethyl oxalacetate, ethanol and acetic acid to obtain 1 - (2 - tetrahydrothiophenesulphone)-3 - carbethoxy - 5 - pyrazolone, and forming the nitroso compound and reducing with tin and hydrochloric acid.  1 - (4 - Aminophenyl) - 3 - carbethoxy - 4-amino - 5 - pyrazolone is prepared by heating together the sodium salt of ethyl oxalacetate, p-nitrophenylhydrazine hydrochloride and ethanol to obtain 1 - (4 - nitrophenyl) - 3 - carbethoxy-5 - pyrazolone, forming the nitroso derivative, and reducing with tin sponge and HCl.  3 - Carbethoxy - 4 - amino - 5 - pyrazolone is prepared by heating together sodium acetate, the sodium salt of ethyl oxalacetate and hydrazine sulphate to obtain 3-carbethoxy-5-pyrazolone, forming the nitroso derivative, and reducing with hydrogen in presence of Raney nickel.  1 - (41 - Phenoxy - 31 - sulphophenyl) - 3-amino - 5 - pyrazolone is prepared by reacting p - phenoxy - m - sulphophenylhydrazine in pyridine with ethyl b -ethoxy:b -iminopropionate, and may be reacted with ethyl lauroyl acetate in pyridine to obtain 11-(41-phenoxy-31-sulphophenyl) - 3 - lauroylacetamido - 5 - pyrazolone.  1 - Phenyl - 4 - amino - 5 - pyrazolone - 3 - 3 - (N-b -hydroxyethylcarboxylic amide) is prepared by heating 1 - phenyl - 3 - carbethoxy - 5 - pyrazolone with ethanolamine to obtain 1-phenyl-5-pyrazolone - (N - b  - hydroxyethylcarboxylic azide), forming the nitroso derivative, and reducing.  1 - Phenyl - 3 - (p - aminophenyl) - 4 - aminopyrazolone is prepared by heating ethyl p-nitrobenzoylacetate with phenylhydrazine to obtain 1 - phenyl - 3 - (p - nitrophenyl) - 5 - pyrazolone, forming the nitroso derivative, and reducing with zinc dust and HCl.  1 - Phenyl - 4 - amino - 5 - pyrazolone - 3 - carboxylic acid azide is prepared by reacting 1-phenyl - 5 - pyrazolone - 3 - carboxylic acid hydrazide with nitrous acid to obtain 1-phenyl-4-isonitroso - 5 - pyrazolone - 3 - carboxylic acid amide and reducing with tin and hydrochloric acid.  1 - p - Sulphophenyl - 3 - carbethoxy - 4 - amino-5-pyrazolone is prepared by reacting 1-p-sulphophenyl-3-carbethoxy-5-pyrazolone with nitrous acid and reducing with tin and HCl.  1 - (4 - Carboxymethoxyphenyl) - 3 - carbethoxy-4 - amino - 5 - pyrazolone is prepared by reacting 4-hydrazinophenoxyacetic acid with the sodium salt of ethyl oxalacetate to obtain 1-(4-carboxymethoxyphenyl) - 3 - carbethoxy - 5 - pyrazolone, reacting this with nitrous acid to obtain 1 - (4 - carboxymethoxyphenyl) - 3 - carbethoxy-4 - isonitroso - 5 - pyrazolone, and reducing with tin and HCl.  1 - (2 - Benzthiazolyl) - 3 - methyl - 4 - amino-5-pyrazolone is prepared by reacting 2-chlorobenzthiazole with hydrazine hydrate to obtain benzthiazolyl-2-hydrazine, reacting with ethyl acetoacetate to obtain 1-(2-benzthiazolyl) - 3-methyl-5-pyrazolone, treating with nitrous acid to obtain 1 - (2 - benzthiazolyl) - 3 - methyl - 4-isonitroso - 5 - pyrazolone, and reducing.  Specification 459,665, [Group IV], is referred to.