GB581695A - Improvements in or relating to the manufacture of 5-amino-acridine compounds - Google Patents

Abstract

5-Aminoacridine compounds which may be substituted in the amino nitrogen atom and in the ring are prepared by reaction between a 5-acridyl ether and an ammonium salt or a salt of a primary or secondary amine in a reaction medium which contains water and subsequent liberation of the free base. The ether may be prepared from the corresponding diphenylamine-2-carboxylic acid and not isolated. An organic solvent such as ethyl alcohol may be present. Examples give the preparation of 5-aminoacridine from 5-methoxyacridine and ammonium chloride or sulphate, 5-methylaminoacridine from 5-methoxyacridine and methylamine hydrochloride, 2-chloro-5-amino-7-methoxyacridine from 2-chloro-5-ethoxy (or amyloxy or tetrahydrofurfuryloxy)-7-methoxyacridine and ammonium isethionate or chloride, 2-chloro-5-ethylamino-7-methoxyacridine from 2-chloro-5-ethoxy (or benzyloxy)-7-methoxyacridine and ethylaminehydroxhlocird, 2-chloro5-benzylamino-7-methoxyacridine lactate from 2- chloro - 5-n-butoxy - 7 - methoxyacridine and benzylamine lactate, and 2-chloro-5-(a -methyl-d -diethylamino-butylamino) -7-methoxyacridine from 2-chloro-5-ethoxy-7-methoxyacridine and a - diethylamino - 8 - aminopentane dihydrochloride. 2-Chloro-5-ethoxy-, -5-n-butoxy-, -5-benzyloxy-, and -5-tetrahydrofurfuryloxy-, 7-methoxyacridine are prepared by the action of sodium ethoxide, n-butoxide, benzyloxide, and furfuroxide on 2,5-dichloro-7-methoxyacridine. 5-Amyloxyacridine is prepared by refluxing diphenylamine-2-carboxylic acid with phosphorus oxychloride and adding a solution of sodium in amyl alcohol.