GB604279A - Production of substituted arylamino acridine derivatives - Google Patents

Abstract

Arylamino acridine derivatives having the general formula <FORM:0604279/IV(b)/1> in which R represents hydrogen or an alkyl, aryl or aralkyl group and n represents an integer not greater than 8 are obtained by heating a meso-halogenated acridine with a primary or secondary arylamine of the general formula <FORM:0604279/IV(b)/2> in which R and n are as above defined. The meso-halogenated acridines are advantageously meso-chloroacridines and may contain one or more nuclear substituents such as alkyl, alkoxy, nitro, amino, substituted amino, cyano or halogen in either or both of the benzenoid nuclei. Specified acridines are: 9-chloroacridine, 9-bromoacridine, 2-methoxy-9-chloroacridine, 2- and 3-cyano-9-chloro-acridines, 2-methoxy-6-cyano-9-chloro-acridine, 2-methoxy-7-cyano - 9 - chloro - acridine, 2 - methoxy - 6.9-dichloroacridine - 2 - methoxy - 6.9 - dibromoacridine and 2-dimethylamino-6.9-dichloroacridine. The primary or secondary arylamine used has the residue -(CH2)n-CN in the p-position with respect to the amino group and there may be p present one or more additional nuclear substituents, viz. alkyl (e.g. methyl, ethyl and isopropyl), alkoxy (e.g. methoxy and ethoxy) and halogen substituents. Specified arylamines are: a para-aminophenyl-acylonitrile, e.g. p-amino-benzyl cyanide; a mono-N-alkyl substituted p-aminophenyl-acylonitrile, e.g. an N-methyl-p-aminophenyl-acetonitrile, or an N-aryl or N-aralkyl-p-aminophenyl-acylonitrile. Advantageously, the reaction takes place in an alkanol solution, the alkanol containing not more than eight carbon atoms, preferably anhydrous, and preferably in the presence of a small amount of copper powder. Alternatively, when R represents hydrogen the reactants may be heated in an excess of a phenol, e.g. phenol, the cresols, or higher alkylated phenols, the meso-halogenated acridine and phenol being first heated together and the product, with or without isolation, is then heated with the primary arylamine. In examples: (1) 9-chloroacridine is dissolved in an excess of molten phenol and the solution treated with p-amino benzyl cyanide to obtain 9-(41-cyanomethylphenyl-amino)-acridine; (2) 2-methoxy-6 : 9-dichloroacridine is heated with an excess of phenol and the mixture is treated with p-amino benzyl cyanide to obtain 2-methoxy-6-chloro-9-(41-cyanomethyl phenylamino)-acridine. The aminophenyl acylonitriles may be obtained by the reduction of the corresponding nitro compounds by known methods.