OXIDATION OF ACETANILIDES TO GLYCOLANILIDES AND OXANILIC ACIDS IN RABBITS

In the urine of rabbits injected with various acetanilides, the corresponding glycolanilides were found. Approximately 5 per cent of the given acetanilides appeared in the urine as 4-chloro-glycolanilide, 4-bromo-glycolanilide and 4-propionyl-glycolanilide. They were isolated and their structures were established by u.v., i.r. and NMR spectra. Less than 1 per cent of acetanilide and phenacetin were excreted as glycolanilides. No 4-propyl-glycolanilide was found in the urine after the administration of 4-propyl-acetanilide. The effect of various substituents in 4-position on the bio-chemical hydroxylation of acetic acid in acetanilides is discussed. Rabbits dosed with 4-chloro-acetanilide or 4-propionyl-acetanilide were found to excrete several per cent of the doses as the corresponding oxanilic acids. © 1969.