Patent GB-816382-A (GB)
Title: Light-sensitive layers for photomechanical reproduction
Inventor: MOORE RALPH GOWER DAVIES
IPC: G03F7/016
Filed: 1957-03-15
Abstract: 5 : 7-Dibrom-2-methylindole, 5 : 7-diphenyl-2-methylindole and 2-methyl-5-phenylindole are prepared by cyclizing the 2 : 4-dibromophenylhydrazone, the m-terphenyl-41-hydrazone and the p-xenylhydrazone respectively of acetone. 2-Phenyl-5-nitroindole is prepared by cyclizing the p-nitrophenylhydrazone of acetophenone. m-Terphenyl-41-hydrazine is prepared by diazotization and reduction of m-terphenyl-41-amine.  m-Terphenyl-41-hydrazone of acetone, p-xenylhydrazone of acetophenone and p-nitrophenylhydrazone of acetophenone are prepared from the corresponding hydrazines.  N - (3 - cyano - 4 - biphenylyl)acetamide is prepared from N-(3-bromo-4-biphenylyl)acetamide according to the procedure of French Patent 828,202.  4 - Amino - 3 - biphenylcarbonitrile is prepared by alkaline hydrolysis of N-(3-cyano-4-biphenylyl)acetamide; 2-amino-1-naphthonitrile is prepared by alkaline hydrolysis of N-(1-cyano-2-naphthyl)acetamide.  3-Amino-5-phenylindiazole is prepared by diazotization and reductive cyclization of 4-amino-3-biphenyl-carbonitrile; 3-aminoindiazole (tin double salt described) is prepared by diazotization and reductive cyclization with stannous chloride of o-aminobenzonitrile; 1-amino-1-benz(e)indiazole is prepared by diazotization and reductive cyclization of 2-amino-1-naphthonitrile; 3-amino-5 : 7-dibromoindiazole is prepared by diazotization and reductive cyclization of 2-amino-3 : 5-dibromobenzonitrile; 3-amino-6-phenylindiazole is prepared by diazotization and reductive cyclization of 3-amino-4-biphenylcarbonitrile. 3-Nitroso-2-methylindole is prepared by nitrosating 2-methylindole; 3-nitroso-2-phenylindole is prepared by nitrosating 2-phenylindole; 2 - p - chlorophenyl - 4 : 5 - diphenyl - 3 - nitrosopyrrole is prepared by nitrosating 5-p-chlorophenyl - 2 : 3 - diphenylpyrrole; 1 : 4 - bis(p - chlorophenyl) - 3 - nitrosopyrrole is prepared by nitrosating 1 : 4-bis(p-chlorophenyl)pyrrole; 5-(4 - biphenylyl) - 2 : 3 - diphenyl - 4 - nitrosopyrrole is prepared by nitrosating 5-(4-bi-o-phenylyl) - 2 : 3 - diphenylpyrrole; N - methyl - 41 - (3 - nitroso - 4 : 5 - diphenylpyrrole - 2) - benzenesulphonanilide is prepared by nitrosating N - methyl - 41 - (4 : 5 - diphenylpyrrole - 2) - benzenesulphonanilide.  3 - Amino - 3 - methylindole, 3 - amino - 2 - phenylindole and 2(3-indolyl)-3-amino-3-pseudoindole are prepared by sodium dithionate reduction of 3-nitroso-2-methylindole, 3-nitroso-2-phenylindole and 2(3 - indolyl) - 3 - nitroso - 3 - pseudoindole respectively.  2(3 - Indolyl) - 3 - isonitroso - 3 - pseudoindole is prepared by treating indole with very dilute nitrous acid.  4 - p - Chlorophenyl - 1 : 2 - diphenyl - 1 : 4 - butanedione is prepared by condensing benzoin with 41-chloroacetophenone; 2-desyl-41-phenylacetophenone is prepared by condensing benzoin with 41-phenylacetophenone; N-methyl-41-desylacetylbenzenesulphonanilide is prepared by condensing benzoin with N-methyl-41-acetylbenzenesulphonanilide.  5 - p - Chlorophenyl - 2 : 3 - diphenylpyrrole is prepared by cyclization of 4-p-chlorophenyl-1 : 2 - diphenyl - 1 : 4 - butanedione; 2 : 5 - bis-(p-chlorophenyl)pyrrole is prepared by cyclization of 1 : 4-bis(p-chlorophenyl)-2-butanedione; 5-(4-biphenylyl)-2 : 3-diphenylpyrrole is prepared by cyclization of 2-desyl-41-phenylacetophenone; N - methyl - 41 - (4 : 5 - diphenylpyrrole-2) - benzenesulphonanilide is prepared by cyclicization of N-methyl-41-desylacetylbensenesulphonanilide.  The cyclizations being conducted in presence of ammonium acetate.  3 - Amino - 2 - p - chlorophenyl - 4 : 5 - diphenylpyrrole is prepared by catalytic reduction of 2 - p - chlorophenyl - 4 : 5 - diphenyl - 3 - nitrosopyrrole; 1 : 4 - bis(p - chlorophenyl) - 3 - aminopyrrole is prepared by catalytic reduction of 1 : 4 - bis - (p - chlorophenyl) - 3 - nitrosopyrrole; 5 - (4 - biphenylyl - 2 : 3 - diphenyl - 4 - aminopyrrole is prepared by catalytic reduction of 5 - (4 - biphenylyl) - 2 : 3 - diphenyl - 4 - nitrosopyrrole; N - methyl - 41 - (3 - amino - 4 : 5 - diphenylpyrrole - 2) - benzenesulphonanilide is prepared by catalytic reduction of N - methyl - 41 - (3 - nitroso - 4 : 5 - diphenylpyrrole - 2) - benzenesulphonanilide.  1 : 4 - Bis - (p - chlorophenyl) - 1 : 4 - butanedione is prepared by dithionate reduction of 1 : 4-bis-(p-chlorophenyl)-2-butene-1 : 4-dione. 41-Acetylbenzenesulphonanilide is prepared by reacting 41-aminoacetophenone with benzene sulphonyl chloride.  N - Methyl - 41 - acetylbenzenesulphonanilide is prepared by methylation of 41-acetylbenzene-sulphonanilide.  2 - Tert. - butyl - 3 - diazo - 3 - pseudoindole, 5 - chloro - 3 - diazo - 2 - methyl - 3 - pseudoindole, 1 - diazo - 2 - phenyl - 1 - benz(e)indole, 3 - diazo - 5 : 7 - dibromo - 2 - methyl - 3 - pseudoindole, 3 - diazo - 5 : 7 - diphenyl - 2 - methyl - 3 - pseudoindole, 3 - diazo - 2 - ethyl - 3 - pseudoindole, 3 - diazo - 2(3 - indolyl) - 3 - pseudoindole, 3 - diazo - 2 - methyl - 3 - pseudoindole, 3 - diazo - 2 - methyl - 5 - phenyl - 3 - pseudoindole, 3 - diazo - 2(2 - naphthyl) - 3 - pseudoindole, 3 - diazo - 5 - nitro - 2 - phenyl - 3 - pseudoindole, 3 - diazo - 2 - phenyl - 3 - pseudoindole, 3 - diazoindole, 1 - diazo - 1 - benz(e)indiazole, 3 - diazo - 5 : 7 - dibromoindiazole, 3 - diazo - 6 - phenylindiazole and 3-diazo-5-phenylindiazole are prepared by diazotizing the corresponding amino compounds.  3 - Diazo - 2 : 4 - diphenyl - 3H - pyrrolenine, 2 - p - chlorophenyl - 3 - diazo - 4 : 5 - diphenyl - 3H - pyrrolenine, 2 : 5 - bis(p - chlorophenyl) - 3 - diazo - 3H - pyrrolenine, 2 - (4 - biphenylyl) - 3 - diazo - 4 : 5 - diphenyl - 3H - pyrrolenine, N - methyl - 41 - (3 - diazo - 4 : 5 - diphenyl - 3H - pyrrolenine - 2 - yl) - benzenesulphonanilide and 3 - diazo - 2 : 4 : 5 - triphenyl - 3H - pyrrolenine are prepared by diazotizing the corresponding 3-aminopyrroles.  4 - Diazo - 2 : 5 - diphenyl - 4H - isoimidazole is prepared by diazotizing 4-amino-2 : 5-diphenylimidazole.