2,3,5-Trimethylpyridine → 2,3,5-Trimethyl-1-oxidopyridin-1-ium

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Reaction Steps

3-Chloro per benzoic acid (10 g, 164.2 mmol) was added to a solution of 2,3,5-trimethylpyridine (10 g, 82.1 mmol) in DCM at 0° C. and the mixture was stirred at RT for 8 h (the reaction was monitored by TLC). The reaction was quenched with sodium bicarbonate solution and stirred for 1 h at RT. The organic layer was separated, dried over sodium sulfate, filtered and concentrated under reduced pressure to afford 2,3,5-trimethylpyridine 1-oxide (6.5 g, 58.0%,) as a brown solid. 1H NMR: 200 MHz, CDCl3: δ 8.15 (s, 1H), 7.15 (s, 1H), 2.55 (s, 3H), 2.35 (s, 3H), 2.25 (s, 3H). MS: [M+H]+: m/z=311.2.

Provenance & Evidence