Kinetics of reactions in heterocycles. Part IX. Trimethylammonio- and dimethylamino-N-methyl-derivatives of quinoline, isoquinoline, cinnoline, phthalazine, quinazoline, and quinoxaline

Abstract

Trimethylammonio-derivatives of quinoline and quinazoline have been prepared: from the corresponding chloro-compound with trimethylamine or by quaternisation of the dimethylamino-compound with methyl iodide. The kinetics of their reactions with hydroxide ion have been measured; quinazolin-4-yltrimethylammonium chloride was found to be ca. 700 times more reactive than 4-chloroquinazoline, at 20°.

Nuclear N-methyl derivatives of dimethylamino-quinoline, isoquinoline, cinnoline, phthalazine, and quinoxaline have been prepared by quaternisation.

Ionization constants, u.v. and ¹H n.m.r. spectra are recorded and discussed.