Sodium Hydroxide → 2-methyl-3-fluoro-4-chloro-pyridine-N-oxide

Participants

Reaction Steps

Phosphoryl chloride (19 ml) in dichloromethane (50 ml) was added dropwise to a stirred solution of 2-methyl-3-fluoro-4-nitropyridine-N-oxide (12 g) in dichloromethane (50 ml). The reaction mixture was heated under reflux for a total of 8 hours. After cooling and pouring onto ice, the mixture was basified (NaOH) to pH 9 and extracted with dichloromethane. After drying (K2CO3) and removal of solvent, the crude product was purified by column chromatography (silica gel; 1% MeOH/CHCl3) to give 2-methyl-3-fluoro-4-chloro-pyridine-N-oxide (6.78 g) m.p. 63°-65°.

Provenance & Evidence