Nitric Acid → 4-Nitro-2,3,5-trimethylpyridine, 1-oxide

Participants

Reaction Steps

To a cooled solution of fuming HNO3 (50 ml) and conc. H2SO4 (50 ml) in an ice bath was added 2,3,5-trimethylpyridine-N-oxide (35.67 g) and the reaction mixture was stirred at 40°-50° C. for 18 h. After which time, the reaction was cooled to rt, poured into water/crushed ice (250 ml), alkalized with NaOH pellets and extracted with CH2 Cl2 (3×100 ml). The extracts were combined and washed with sat. NaCl (1×50 ml), dried (MgSO4) and the solvent removed in vacuo to give 4-nitro-2,3,5-trimethyl-pyridine-N-oxide (45.5 g, 96%) as an orange solid; mp 69°-71° C. (ether), orange plates.

Provenance & Evidence