Patent GB-843497-A (GB)
Title: Improvements in colour photography
IPC: C07D231/52
Filed: 1956-11-30
Abstract: 2;4 - Dichloro - 3 - methyl - 6 - [ a  - ( 3- n - pentadecylphenoxy) acetamido] phenol is prepared by adding a -(3-n-pentadecylphenoxy) acetyl chloride to a mixture of 6-amino-2;4-dichloro-3-methylphenol hydrochloride and sodium acetate in acetic acid.  The same aminophenol may be reacted with a - or g -(3-n-pentadecylphenoxy) butyryl chloride, a -or g -(2;4-di-n-amylphenoxy)-n-butyryl chloride, a -(2-n-octyl-4-n-amylphenoxy -n-butyryl chloride or a -(4-n-octylphenoxy) acetyl chloride instead of the above acetyl chloride.  Similarly, 2-caprylylamido-5-aminophenol, a -(m-aminobenzoyl-2-methoxy-acetanilide hydrochloride or a -benzoyl-5-amino-2-methoxyacetanilide may be reacted with a -(3-n-pentadecylphenoxy) - n - butyryl chloride, the former reaction being carried out in quinoline and dioxane, however.  a -(3-n-Pentadecylphenoxy) acetic acid is prepared by treating the potassium salt of 3-n-pentadecylphenol in xylene with sodium chloroacetate and acidifying the product with hydrochloric acid. Treatment with thionyl chloride gives the acid chloride. Similarly, the above phenol potassium salt may be reacted with ethyl a - or g - bromobutyrate, or the sodium salt of p-n-octyl phenol may be reacted with sodium chloroacetate and the acids converted to the corresponding acid chlorides.  2-caprylylamido-5-nitrophenol is prepared by adding octanoyl chloride to 2-amino-5-nitrophenol and quinoline in dioxane.  The product is reduced to the corresponding amino compound by hydrogenation with a nickel catalyst.  a -Benzoyl-2-methoxy-5-nitroacetanilide is prepared by reacting 4-nitro-2-aminoanisole with ethyl benzoylacetate.  The product is reduced to the corresponding amino compound by hydrogenation with a nickel catalyst.  a  - (m - Nintrobenzoyl) - methoxyacetanilide is prepared by refluxing ethyl a -(m-nitrobenzoyl) acetate with o-anisidine in xylene.  It is converted to the corresponding amino compound by reaction with aqueous sodium sulphide in ethanol.  1 - Hydroxy - 2 - [ a (3 - n - pentadecylphenoxy)-n-butyl] naphthamide is prepared anologously to compound 1 of Specification 649,660 by condensing 3-n-pentadecyl-phenol with g -chlorobutyronitrile in alkali, reducing the nitrile to the butylamine and condensing the product with 1-naphthol-2-carboxylic acid phenyl ester.  1 - (21; 41; 61 - Trichlorophenyl) - 3 - [a  - (3-n - pentadecyl-phenoxy) butyrylamido] - 5 - pyrazolone is prepared in the same way as coupler 9 of Specification 680,448 by condensing a -(3 - n - pentadecylphenoxy) - n - butyryl chloride with the appropriate 3-amino-5-pyrazolone.  The corresponding 1-(21;41;51;-trichlorophenyl)-e pyrazolone is similarly prepared.  1 - (21:41;61 - Trichlorophenyl) - 3 - \sT 311-[a  - (3 - n - pentadecylphenoxy) - n - butyrylamido] benzarmido \sV - 5 - pyrazolone is prepared in the same way as coupler 7 of Specification 680,488 by reacting the 1-substituted -3-amino-5-pyrazolone with m-nitrobenzoyl chloride, reducing the nitro group to an amino group and condensing with a -(3-n-pentadecylphenoxy)-n-butyryl chloride. The 1-(21;41;51-trichlorophenyl)- compound may be similarly prepared 1-(21:41;-51-trichlorophenyl - 3 - \sV311 - [g -(2111;4111 - di - n - amylphenoxy) - n butyrylamido] benzamido \sV - 5 - pyrazolone may be similarly prepared from g -(2;4-di-n-amylphenoxy) -n-butyryl chloride.  a  - \sT 3 - [g  - (2; 4 - Di - amylphenoxy) butyrylamido] benzoyl \sV - 2 - methoxyacetanilide is prepared in the same way as compound IV of Specification 800,108 by reacting a -(m-aminobenzoyl)-2-methoxy acetanilide hydrochloride with g -(2;4 - di - n - amylphenoxy) - n - butyryl chloride.  Instead of the latter chloride, a -(2;4 - di - n - amylphenoxy) n - butyryl chloride, a  - (2 - n - octyl - 4 - n - amylphenoxy) - n - butyryl chloride, a  - (2 - methyl - 4 - n - decyl - phenoxy) - n - butyryl chloride or a  - (2 - n - decyl -4-methylphenoxy) - n - butyryl chloride may be used. Specification 791,219 also is referred to.