Changes undergone by 2-amino-N-(pyridyl-3′) anilinesunder pschorr reaction conditions

Reaction of 2 -nitroaniline with 3 -brornopyridine, 3 -iodo-5 -methylpyridine, and 3-iodo-6-methylpyridine gives 54–73% yield of the hitherto unknown 2-nitro-N-(pyridyl-3) aniline, 2-nitro-N-(5 -methylpyridyl3) aniline, and 2-nitro-N-(6-methylpyridyl-3) aniline. The nitro compounds prepared can easily be reduced to the corresponding amino-N-pyridylanilines. The amino compounds do not form carbolines under Pschorr reaction conditions, but are converted to triazoles or N -(pyridyl-3)-aniline.