2,5-Dimethylpyridine → 2,5-Dimethylpyridin-1-ium-1-olate

Participants

Reaction Steps

To a solution of 2,5-dimethylpyridine (2.24 g, 21 mmol) in CHCl3(20 mL) was added MCPBA (4.31 g, 25 mmol) in portions over 30 min. The mixture was stirred at room temperature overnight. Calcium hydroxide (4 g, 54 mmol) was added to quench the reaction and the mixture was stirred vigorously for 3 h. The mixture was filtered through a Celite pad. The filtrate was concentrated and dried under vacuum to give 2,5-dimethylpyridine 1-oxide (2.5 g, 97.1% yield) as white solid, which was used without purification. CMS retention time 0.442 min; LCMS MH+ 124.

Provenance & Evidence