GB541328A - Improvements relating to the use of substituted aromatic diamines in photography - Google Patents

Abstract

541,328. Aromatic nitrogen derivatives. KODAK, Ltd. (Eastman Kodak, Co.). Feb. 19, 1940, No. 3112. [Class 2 (iii)] [Also in Group XX] N-Ethyl N-acetonylaniline is prepared by reacting N-ethylaniline and chloroacetone in the presence of sodium bicarbonate. N-Ethyl N-acetonyl-p-phenylenediamine is prepared by the reduction of a methyl alcohol solution of 4 (2<SP>1</SP>-chlorobenzeneazo)-N-ethyl: N- acetonylaniline (obtained by coupling diazotized o-chloraniline with N-ethyl N-acetonylaniline) by the addition of sodium thereto, the ochloroaniline being removed by steam-distillation. The corresponding m-methyl-N-ethyl compound is prepared by reduction of the corresponding p-nitro compound by hydrogen in the presence of nickel. The corresponding m-methyl-p-amino-m-methylphenyl- N -methylaminomethylethylketone is similarly prepared. p- Nitrophenyl-N-ethyl-glycineamide is prepared by nitrating N-ethyl-phenylglycineamide below 45‹C. Reduction by hydrogen in the presence of nickel gives p-aminophenyl-N- ethyl-glycineamide. The compounds p-amino-mmethylphenyl-N-#-hydroxyethylglycineamide, paminophenyl- N-methyl-glycineamide, and pamino-m-methylphenyl- N - methoxyethyl - glycineamide are similarly prepared. The compounds 2-amino-4-hydroxy-1-cyclohexyl - (# - propion - #- hydroxethyl-amide)-amino-naphthalene and N- tetrahydrofurfurylamino - 2 - hydroxy - 4 - aminophenylglycinehydrazide are similarly prepared. Methyl p-aminophenyl-N-ethyl-aminoacetate is prepared by the reduction of the corresponding p-(o-chlorobenzeneazo) compound. 2-Amino- 4-hydroxy 1 - cyclohexyl- (#-propion- #-hydroxy ethylamide)- (amino)-naphthalene is prepared by heating 4-hydroxy-2-nitro-1-naphthylamine with cyclohexyl bromide in benzene in the presence of sodium bicarbonate, heating the product with acrylonitrile in toluene, forming the methyl ester by heating with methyl alcohol and sulphuric acid, forming the amide by re-action with ethanolamine, and reducing by hydrogenation in the presence of nickel. N - Tetrahydrofurfurylamino - 2 - hydroxy - 4 - aminophenylglycinehydrazide is prepared by re-acting 3-nitro-6-chlorophenol with -tetrahydrofurfurylamine, reducing by hydrogenation in the presence of nickel, forming an ester by re-action with methylchloracetate, and reacting with hydrazine hydrate. Methyl paminophenyl- N-ethyl-aminoacetate is prepated by the reduction of the corresponding p-(ochlorobenzeneazo) compound, in ethyl alcohol solution by hydrogenation in' the presence of nickel, the two amines produced being separated by fractional distillation under reduced pressure. The p-(o-chlorobenzeneazo) compound is prepared by re-acting N-ethyl-aniline and methylchloracetate in the presence of sodium bicarbonate and then coupling with diazotized o-chloraniline. Amino-m-methylphenyl - N - ethylglycineamide is prepared by reacting m-toluidine and chloracetamide in the presence of sodium carbonate, N-ethylating with diethylsulphate, and either diazotizing or coupling with diazotized sulphanilic acid, followed by reduction.