GB623997A - Manufacture of new dyestuff intermediates of the anthraquinone series - Google Patents

Abstract

Anthraquinone derivatives carrying one or more pendant aryl groups attached directly or through -O-, -S-, -CO.NH-, or -NH- linkages are chloro- or bromo-methylated with dichloro- or dibromo-dimethylether in presence of sulphuric acid or aluminium chloride. The ether may be formed in situ from paraformaldehyde and the aluminium chloride or hydrogen chloride. A tertiary base (e.g. pyridine) may be used with the aluminium chloride. The starting materials may be anthraquinone derivatives with or without condensed rings and having the pendant aryl group attached as indicated to the anthraquinone nucleus or to a condensed ring. In examples, the following substances are chlormethylated: (1) sodium 1 - amino - 4-anilino or p-toluidino-anthraquinone-2-sulphonate; (2) 1,4-dianilinoanthraquinone; (3) 1.4 - di - p - toluidinoanghraquinone; (4) 1.4-di - m - xylidinoanthraquinone; (5) 1 - amino-4 - anilino - or p - toluidino - 2 - methyl-anthraquinone; (6) 2-bromo-1-amino-4-anilino anthraquinone; (7) 1-methylamino-4-anilino-or p - toluidino - anthraquinone; (8) 6 - p - toluidino - 3 - methyl - 11.91 - anthrapyridone; (9) 6 - p - toluidino - 11.91 - anthrapyrimidine; (10) 6 - p - butylanilino - 2 - phenyl - 11.91-anthrapyrimidine; (11) 6-anilino-11.91-anthrapyrimidone; (12) 8.17-di-p-toluidinoindanthrone; (13) 2-anilino-3-hydroxy-11.21-pyrazinoanthraquinone; (14) 2.8-diphenylanthraquinone - 11.21 - (N) - 51. 61 - (N) - dithiazole; (15) 1 - hydroxy - or 1.5 - dihydroxy - 4-anilinoanthraquinone; (16) 1.4-diamino-2-phenoxyanthraquinone; (17) 2 - phenyl - 6-anilino- or p-toluidino-11.91-anthrapyrimidine; (18) 6-anilino-11.91-anthrapyrimidine; (19 1.4-diamino - 2.3 - di - (p - tolymercapto) - anthraquinone; (20) anthraquinone-2-carboxylic acid anilide. Also in examples: (21) 1.4-di-p-toluidinoanthraquinone, and (22) 6-p-toluidino-3-methyl-11.91-anthrapyridone are bromomethylated.