m-Chloroperbenzoic acid → 2-(Methoxycarbonyl)-3-methylpyridine 1-oxide

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Reaction Steps

A mixture of methyl 3-methylpicolinate (2 g, 14.8 mmol) and m-CPBA (3 g, 17.8 mmol) in DCM (35 mL) was stirred at RT overnight. Then the mixture was washed with NaHSO3 (a.q.) and concentrated in vacuum. The residue was purified by column chromatography (DCM:MeOH=200:1) to give the product of 2-(methoxycarbonyl)-3-methylpyridine 1-oxide (1.89 g, yield: 79%). 1H-NMR (CDCl3, 400 MHz) δ 8.05 (d, J=6.0 Hz, 1H), 7.18 (t, J=8.4 Hz, 1H), 7.10 (d, J=8.0 Hz, 1H), 3.95 (s, 3H), 2.23 (s, 3H). MS (M+H)+: 168.

Provenance & Evidence