m-Chloroperbenzoic acid → 2-Chloro-6-methylpyridine 1-oxide

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-chloro-6-methylpyridine (60.0 g, 0.47 mol) in CH2Cl2 (500 mL) was added m-CPBA (122 g, 0.700 mol), and the reaction mixture was stirred at 40° C. for 8 hours. The reaction was quenched with sodium thiosulfate and adjusted to pH=7.5 with sodium bicarbonate solution. The organic layer was washed with water, dried over sodium sulfate and the solvent was evaporated to afford 2-chloro-6-methylpyridine 1-oxide. 1H NMR (300 MHz, CDCl3) δ 7.37 (dd, J1=8.1 Hz, J2=1.5 Hz, 1H), 7.18 (dd, J1=7.8 Hz, J2=1.5 Hz, 1H), 7.07 (t, J=7.8 Hz, 1H), 2.54 (s, 3H). LRMS calc'd for (C6H6ClNO) [M+H]+, 144; found 144.

Provenance & Evidence