Sodium Methoxide → 4-Methoxy-2,3,5-trimethylpyridine 1-oxide

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Reaction Steps

To a solution of sodium methoxide, prepared from Na (8.62 g, 0.375 mol) and MeOH (500 ml), was added 4-nitro-2,3,5-trimethylpyridine-N-oxide (45.5 g, 0.25 mol). The reaction mixture was refluxed for 5 h, cooled to rt and most of the solvent removed in vacuo. The slurry was diluted with water (100 ml) and extracted with CH2Cl2 (3×100 ml). The extracts were combined, washed with sat. NaCl solution, dried (MgSO4) and the solvent removed in vacuo to give 4-methoxy-2,3,5-trimethylpyridine-N-oxide as a semi-solid (37.5 g, 90%).

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