Patent GB-843940-A (GB)
Title: Method of processing photographic silver halide emulsions containing colour couplers
IPC: G03C7/32
Filed: 1956-09-26
Abstract: 1-Hydroxy - N - [3 - (4-methoxyphenylglyoxylyl) phenyl]-2-naphthamide is prepared by mixing phenyl 1-hydroxy-2-naphthoate with 3-amino-41-methoxybenzil and heating on an oil bath.  Similarly, phenyl 1-hydroxy-2-naphthoate is reacted with di-dodecyl-5-amino-isophthate to give 1-hydroxy-2-(31,51-bis-dodecyloxycarbonyl) naphthanilide which may then be heated with conc sulphuric acid to give the corresponding 4-sulpho derivative.  1 - Hydroxy - N - [4 - \sT 3 - [a -(3:5 - dicarbomethoxyphenoxy)acetamido]phenyl - glyoxylyl \sV phenethyl]-2-naphthamide is prepared by treating a mixture of 4-(b -aminoethyl)-31-nitro-benzil hydrochloride and triethylamine in dioxane with 1-hydroxy-2-naphthoyl chloride in dioxane, followed by reduction of the nitro group to give 1 - hydroxy - N - [4 - (3 - aminophenylglyoxylyl) phenethyl] - 2 - naphthamide.  The latter is then treated with 3;5-dicarbomethoxy phenoxyacetyl chloride in dioxane in the presence of triethylamine.  Tetradecyl - 1 - hydroxy - 4 - sulpho - 2 - naphthoate monohydrate is prepared by treating tetradecyl 1-hydroxy -2-naphthoate with conc. sulphuric acid.  1 - Hydroxy - N - (b  - stearoyloxyethyl) - 2 - naphthamide is prepared by reacting phenyl 1-hydroxy-2-naphthoate with ethanolamine by heating on a steam bath to give 1-hydroxy-N-(b -hydroxyethyl)-2-naphthamide, which is then reacted with stearoyl chloride.  1 - Hydroxy - N - { b  - [3 - (octadcyloxy carbonyl) phenyl - sulphonamido] - ethyl } - 4 sulpho - 2 - naphthamide is prepared by reacting phenyl 1 - hydroxy - 2 - naphthoate with ethylene diamine to give 1 - hydroxy - N - (b  - aminoethyl)-2 - naphthamide, which is then reacted with octadecyl - m - chlorosulphonyl benzoate in pyridine to give 1 - hydroxy - N - { b  - [3 - (octadecyloxy - carbonyl) phenylsulphonamido] - ethyl } - 2 - naphthamide.  The latter is then sulphonated with conc. sulphuric acid.  1 - Hydroxy - 4 - chloro - N - [b  -(3 - dodecyloxysulphonyl - benzamido) - ethyl] - 2 - naphthamide is prepared by reacting phenyl - 4 - chloro - 1 - hydroxy - 2 - naphthoate with ethylenediamine to give 1 - hydroxy - N - (b  - aminoethyl) - 4 - chloro - 2 - naphthamide, condensing the latter with m-chlorosulphonylbenzoyl chloride to give 1 - hydroxy - 4 - chloro - N - [b  - (3 - chlorosulphonylbenzamido) - ethyl] - 2 - naphthamide and treating this with lauryl alcohol in pyridine.  Octadecyl - m - chlorosulphonyl benzoate is prepared by heating m - chlorosulphonyl benzoyl chloride with octadecyl alcohol.  Di - dodecyl 5 - nitro - isophthalate is prepared by treating 5 nitro - isophthalic acid with thionyl chloride to give the acid chloride which is then heated with lauryl alcohol.  The nitro group in the product may be reduced to the corresponding amine with hydrogen under pressure and a nickel catalyst.  3 - nitrophenylacetyl chloride is prepared by treating the acid with thionyl chloride.  The product may be condensed with anisole or N - phenethyl-acetamide in carbon disulphide in the presence of aluminium chloride to give respectively a  - (3 - nitrophenyl) - 4 - methoxy - aceto - phenone or a  - (3 - nitrophenyl) - 4 - (p - acetamido ethyl acetophenone.  Similarly, the acid chlorides of m - and p - cyanophenylacetic acid are prepared and reacted with benzene instead of anisole as above to give a  - (m - or p - cyano - phenyl) - acetophenone.  4 - methoxy - 31- nitrobenzil is prepared by oxidising a  - (3 - nitrophenyl) - 4 - methoxy - acetophenone by boiling with selenium dioxide in dioxane and a little water.  The nitro group in the product may be reduced to the corresponding amine.  4 - (b  - acetamido - ethyl) - 31 - nitrobenzil may be similarly prepared, and the product boiled with conc-hydrochloric acid to give 4 - (b  - aminoethyl) - 31 - nitrobenzil hydro - chloride.  Similarly, m - or p - cyanobenzil is prepared from a  - (m - or p - cyanophenyl) acetophenone, the cyano group then being hydrolyzed to the corresponding carboxylic acid by means of sulphuric acid, and the acid chloride formed by boiling with thionyl chloride.  1 - { 4 - [4 - (Phenylglyoxylyl) benzamido] phenyl } - 3 - butyramido - 5 - benzoyloxy - pyrazole is prepared by adding benzil - p - carboxylic acid chloride to 1 - (p - aminophenyl) - 3 - butyramido - 5 - benzoyloxy - pyrazole and sodium acetate in glacial acetic acid.  1 - (21, 41, b-Trichlorophenyl) - 3 - { 3 - [3-(phenyl-glyoxylyl)-benzamido] benzamido } - 5 - benzoyloxy - pyrazole is similarly prepared from benzil - m - carboxylic acid chloride and 1 - (2; 4; 6-trichlorophenyl) - 3 - (m - amino - benzamido) - 5 - benzoyloxy - pyrazole.  a  - (p - Nitrobenzoyl) - 3 - (p - methoxy phenyl - glyoxylyl) acetanitide is prepared by adding 3 - amino - 41 - methoxybenzil in xylene to a boiling solution of ethyl p - nitribenzoyl acetate in xylene Specifications 524,154, 524,554, 524,555, 524,557 and 541,589 are referred to.