The oxidative amination of 3-nitropyridines

3-Nitropyridine was reacted with ammonia or alkylamines and KMnO4 under sev eral different conditions. Substitutions in the pura posit ion to the nitro group were obtained with high regio selectivity: with ammonia, 2-amino-5-n itropyridine (66%), with butylamine, 2-butylamino-5-nitropyridine (92%), wi th diethylamine, 2-diethylamino-5-nitropyridine (49%). Under the same condi tions, with methyl-3-nitroisonicotinoate and diethylamine/KMnO4, methyl 2-d iethylamino-5-nitroisonicotinoate (48%), with 4-acetyl-3-nitropyridine (pro tected by ethylene glycol) 2-diethylamino-4-acetyl-5-nitropyridine (72%, pr otected) and with 4-cyano-3-nitropyridine, 2-amino-4-cyano-5-nitropyridine (41%) were obtained. All yields are isolated. (C) 2001 Elsevier Science Ltd . All rights reserved.