Patent GB-733119-A (GB)
Title: Photographic colour couplers
IPC: G03C7/36
Filed: 1953-07-29
Abstract: Amides of the general formula <FORM:0733119/IV (b)/1> are described, wherein X represents -NHCO-, -(CH2)pCONH- where p is 0 to 4, -OCH2 CONH-, -O(CH2)3CONH- or -CH = CH CONH-, Z represents an alkyl group or an alkali metal, n is 0 or 1, radical I is connected to X in meta or para position and radical II carries the substituents shown in positions other than para to X. (4-Methoxybenzoyl)-4-{a -[2-(2 : 4 - di-tert. - amylphenoxy) - 5 - (3 : 5 - dicarbomethoxyphenyl carbamyl) phenyl carbamyl] methoxy} - acetanilide is prepared by reacting ethyl p-methoxy benzoylacetate with methyl 5 - [4 - (2 : 4 - di-tert. - amyl phenoxy)-3 - (4 - amino phenoxyacetamido) benzamido] isophthalate. Other compounds of the formula above are produced in a similar manner by reacting the appropriate intermediates (see below) with ethyl o-methoxybenzoyl acetate.  (2 - Methoxybenzoyl) - 4 - [3 - (3 : 5 - dicarbomethoxy phenyl carbamylvaleramido)-6-(2 : 4-di-tert. - amylphenoxy) benzamido] acetanilide is made by reacting (2 - methoxybenzoyl) - 4-[3 - amino - 6 - (2 : 4 - di - tert. - amylphenoxy) benzamido] acetanilide with 3 : 5-dicarbomethoxyphenylcarbamylvaleryl chloride.  The alkali metal salts of the above compounds may be obtained by hydrolysing the esters with, for example, sodium hydroxide.  Methyl - 5 - [4 - (2 : 4 - di - tert. - amylphenoxy)-3 - (4 - aminophenoxyacetamido)benzamido] isophthalate is prepared by reducing the corresponding 4-nitrophenoxyacetamido compound with hydrogen and Raney nickel. Methyl - 5 - [4 - (2 : 4 - di - tert. - amylphenoxy)-3 - (4 - nitrophenoxyacetamido) benzamido] isophthalate is prepared by reacting p - nitrophenoxyacetyl chloride with methyl-5-[4-(2 : 4-di-tert.-amylphenoxy) - 3 - aminobenzamido] isophthalate. Similar compounds are obtained by using, in place of the p-nitrophenoxyacetyl chloride, p-nitrobenzoyl chloride, m-nitrobenzoyl chloride, m-nitrocinnamoyl chloride or in general, a compound of the formula NO2.  C6H4.Y where Y is the acid chloride corresponding to the amide groups specified above for X, and the nitro compounds produced are reduced to the corresponding amino compounds and reacted with o-methoxy benzoyl acetate to give the compounds of the general formula as described above.  Methyl - 5 - [4 - (2 : 4 - di - tert. - amylphenoxy)-3-aminobenzamido] isophthalate is prepared by reducing the corresponding 3-nitrobenzamido compound with iron and acetic acid.  Methyl - 5 - [4 - (2 : 4 - di - tert. - amylphenoxy)-3 - nitrobenzamido] isophthalate is prepared by reacting 4(2 : 4 - di - tert. - amylphenoxy) - 3-nitrobenzoyl chloride with methyl 5-amino-isophthalate.  3 : 5 - Dicarbomethoxyphenylcarbamylvaleryl chloride is obtained by adding thionyl chloride to the corresponding acid.  (2 - Methoxybenzoyl) - 4 - [3 - nitro - 6 - (2 : 4-di - tert. - amylphenoxy) benzamido] acetanilide is obtained by reacting o-methoxybenzoylacet-4-amino anilide with 2-(2 : 4-di-tert.-amylphenoxy)5 - nitrobenzoyl chloride, and the nitro compound is reduced to the corresponding 3-amino compound with iron and acetic acid.  o - Methoxybenzoylacet - 4 - nitroanilide is prepared by reacting p-nitroaniline with o-methoxybenzoylacetate. The nitro group is then reduced to amino with iron and acetic acid. Ethyl o - methoxybenzoylacetate is obtained by reacting methyl o-methoxybenzoate with ethyl acetate in the presence of sodium.