N-(halo-aryl)-2-methyl-5-alkoxy-indole-3-aceticacids with a - acetic acids with antiphlogistic activity

摘要

1-(Halo-aryl)-2-methyl-5-alkoxy-indole-3-acetic acids with antiphlogistic activity. Title cpds. are produced as follows: p-benzoquinone is reacted with a beta-(N-halophenyl-amino)-crotonic acid ester, the resulting 1-(halophenyl)-2-Me-5-OH-indole-3-carboxylic acid ester is alkylated to the corr. 5-alkoxy cpd. which is saponified with molten alkali to the corr. carboxylic acid, and this is decarboxylated to give a 1-(halophenyl)-2-Me-5-alkoxy-indole; this is subjected to Mannich reaction with HCHO and a secondary amine and the resulting Mannich base is reacted with an alkylating agent to give the corr. quaternary sa this is heated in an alkali cyanide soln. to give the corr. subst. indole-3-acetonitrile, and this is saponified with alkali hydroxide to yield the required 1-(halophenyl)-2-Me-5-alkoxy-indole-3-acetic acid. The end-products and the intermediate nitriles and quarternized Mannich bases are claimed per se.