GB454525A - Process of preparing substituted and unsubstituted amino-m-phenanthrolines in which the amino-group is in the benzene nucleus of the phenanthroline ring system - Google Patents

Abstract

Amino-m-phenanthrolines in which the amino group is in the benzene nucleus of the phenanthroline ring system and which have an anodyne, bactericidal, or therapeutic value are made by reacting a halogen-m-phenanthroline with ammonia or a primary or secondary amine such as an alkylamine, or by reduction of nitro-m-phenanthrolines, or by conversion of m-phenanthroline carboxylic acid amides according to the Hofmann reaction. Amino-m-phenanthrolines substituted in the amino group are made by reacting the unsubstituted compounds with acylating agents such as carboxylic acids or their anhydrides or halides, or with halogen substituted carboxylic acids, alkyl halides or alkylaminoalkylhalides. Compounds of the types specified are acetic, propionic, butyric, benzoic, and chloracetic acids, acetic anhydride, acetyl, benzoyl, and chloracetyl chlorides, ethyl and propyl chlorides and ethyl bromide. In examples: (1) 6-amino-m-phenanthroline is made by reduction of 6-nitro-m-phenanthroline; (2) 5-amino-m-phenanthroline is obtained from 5-bromo-m-phenanthroline (cf. Specification 454,526) and ammonia, is acetylated in (3) benzoylated in (4), and treated with chloracetic acid in (5); (6) 5-bromo-m-phenanthroline is treated with diethylamine to give 5-diethylamino-m-phenanthroline; (7) 5-amino-m-phenanthroline is treated with ethyl bromide to give 5-ethylamino-m-phenanthroline which is treated with more ethyl bromide in (8) to give 5-diethylamino-m-phenanthroline; 5-amino-m-phenanthroline is treated in (9) with b -diethylaminoethylchloride hydrochloride (cf. Specification 167,781, [Class 2 (iii)]), and in (10) with a - diethylaminopropylchloride hydrochloride and in (11) with b -dimethyl-amino-ethyl chloride hydrochloride; (11) 5-m-phenanthroline carboxylic acid is converted to its amide and subjected to the Hofmann reaction.