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.