Patent GB-336428-A (GB)
Title: Manufacture of arylides of aromatic hydroxy-carboxylic acids
Filed: 1929-10-14
Abstract: 336,428. Groves, W. W., (I. G. Farbenindustrie Akt.-Ges.). Oct. 14, 1929. Arylides of m-arylaminephenolcarboxylic acids obtained according to Specification 333,783 are made by reaction of the carboxylic group-with or without previously acylating the nitrogen atom -with an arylamine in the presence of an acid condensing agent, for example phosphorus trichloride, and a diluent, such as xylene, toluene, chlorbenzene and dimethylaniline. Alternatively the carboxylic acid is first converted to the acid chloride by a reagent such as thionyl chloride and then condensed with an arylamine in the presence of a diluent. Products are described from the following pairs of materials :-3- hydroxydiphenylamine carboxylic acid and aniline, o-toluidine, p-toluidine, o-anisidine, dianisidine, #-naphthylamine, p-nitraniline, 1 : 5-diaminonaphthalene; 2<1>-methyl-3-hydroxydiphenylamine carboxylic acid and aniline, #-naphtylamino-paminophenol, p-nitraniline; 3<1>-methyl-3-hydroxydiphenylamine carboxylic acid and aniline, #- naphthylamine, p-nitraniline, 4<1>-methyl-3-hydroxy diphenylamine carboxylic acid and aniline, maminophenol, p-aminophenol, p-nitraniline; 2'- chloro-3-hydroxydiphenylamine carboxylic acid and aniline, o-anisidine, m-aminophenol, pnitraniline; 3<1>-chloro-3-hydroxydiphenylamine carboxylic acid and aniline, o-anisidine, #- naphthylamine, p-nitraniline; 4<1>-chloro-3-hydroxydiphenylamine carboxylic acid and aniline, otoluidine, p-toluidine, o-anisidine, p-anisidine, #- naphthylamine, 1-aminoanthraquinone, 2-aminoanthraquinone, 1.5-diaminoanthraquinone, 3- aminocarbazole, m-aminophenol, p-aminophenol, m-nitraniline, p-nitraniline, p-phenetidine, 2- chloro-p-nitraniline, 6-chloro-p-nitraniline, 2.5- dichloraniline, 4-chlor-2-aminotoluene, 5-chlor-2- aminotoluene, 5-nitro-2-aminotoluene, 5-chlor-2- amioanisole, 4-nitro-2-aminoaniside, 6-amino-3- hydroxy-1-methylbenzene, o-chloraniline, p-chloraniline; 2'-methoxy-3-hydroxy-diphenylamine carboxylic acid and aniline, m-aminophenyl, paminophenol, p-nitraniline; 41-methoxy-3- hydroxydiphenylamine carboxylic acid and aniline; p-nitraniline; 4<1>-phenoxy-3-hydroxydiphenylamine carboxylic acid and #-naphthylamine, p-nitraniline; 2<1>-4<1>-dimethyl-3-hydroxydiphenylamine carboxylic acid and aniline, pnitraniline; 2' - 5<1> - dimethyl-3-hydroxydiphenylamine carboxylic acid and aniline, p-naphthylamine, p-nitraniline; 2'-4'-dichlor-3-hydroxydiphenylamine carboxylic acid and aniline, #- naphthylamine, p-nitraniline; 3'-4'-dichlor-3- hydroxydiphenylamine carboxylic acid and aniline, #-naphthylamine, p-nitraniline; 2'- methyl-5-chloro-3-hydroxydiphenylamine carboxylic acid and aniline, p-nitraniline; 3<1>-methyl- 4<1>-chloro-3-hydroxydiphenylamine carboxylic acid and aniline, o-anisidine, p-anisidine, p-nitraniline; 4<1>-methyl-3<1>-chloro-3-hydroxydiphenylamine carboxylic acid and aniline, #-naphthylamine, pnitraniline, 4-chlor-2-aminotoluene, 5-nitro-2- aminotoluene; 3<1>-methyl-4<1>-methoxy-3-hydroxydiphenylamine carboxylic acid and aniline, pnaphthylamine, p-nitraniline; 3<1>-4<1>-dichloro-6<1>- methyl-3-hydroxydiphenylamine carboxylic acid and p-nitraniline. Aminocresols and aminonaphthols are also mentioned as suitable starting arylamines.