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

Participants

Reaction Steps

To a dichloromethane (dehydrated) (150 ml) solution of a 2,3,5-collidine (11.0 g, 90.8 mmol), 3-chloroperbenzoic acid (24.8 g, 93.4 mmol as the content was regarded as 65%) was added at 1° C. in a nitrogen atmosphere. The mixture was stirred while the temperature was gradually raised to room temperature for 13.5 hours. After the reaction mixture was concentrated, the residue was purified by silica gel column chromatography (NH silica gel: 200 g, elution solvent: heptane/ethyl acetate=50/50, ethyl acetate, ethyl acetate/methanol=20/1) to obtain a crude product of the title compound as a pale yellow oil. After the crude product was diluted with ethyl acetate and a saturated aqueous solution of sodium hydrogen carbonate, the mixture was concentrated. The residue was purified by silica gel column chromatography (NH silica gel: 300 g, elution solvent: heptane, heptane/ethyl acetate=50/50, ethyl acetate, ethyl acetate/methanol=20/1) to obtain the title compound (11.0 g, yield: 88.3%) as a white solid.

Provenance & Evidence