Abstract
Reactions of chloro-2, 6-lutidines and their N-oxides with liquid ammonia in the presence of potassium amide proceed via a hetaryne mechanism to give 3-and 4-amino compounds. Amination of 3- as well as 4-chloro-2, 6-lutidine affords 3-amino-2, 6-lutidine as the main product (13∼15%) with a small amount of the 4-amino isomer. In the case of amination of their N-oxides, mole ratio of the resulting amino isomers is reverse to that in the case of chlorolutidines. 3-Chloro-2, 6-lutidine 1-oxide forms 4-amino-2, 6-lutidine 1-oxide as the main product (50%) with the 3-amino isomer as a by-product (13%), and reaction of 4-chloro-2, 6-lutidine 1-oxide gives 4-amino compound (34%) and the 3-amino isomer (6.5%).
