Hydrogen Peroxide → 3-Isopropyl-2-methyl-1-oxidopyridin-1-ium

Participants

Reaction Conditions

Reaction Steps

A 50% solution of hydrogen peroxide (24.89 mL) was slowly added to a solution of 3-isopropyl-2-methyl-pyridine (24.5 g, 183 mmol) (Ishiguro, et al., Yakugaku Zasshi (1958) 78:220) in HOAc (280 mL). The mixture was warmed to 70° C. and stirred for 18 h, then cooled to room temperature and concentrated in vacuo to remove the majority of HOAc. The mixture was basified with a saturated solution of NaHCO3 to pH 12 and extracted with CH2Cl2 (3×150 mL). The combined organic layers were dried over Na2SO4 and concentrated in vacuo to afford 3-isopropyl-2-methyl-pyridine 1-oxide (26.05 g, 94%) as a yellow oil. 1H NMR (CDCl3) δ 1.24 (d, 6H, J=7.0 Hz), 2.56 (s, 3H), 3.13 (sep, 1H, J=7.0 Hz), 7.06-7.17 (m, 2H), 8.17 (d, 1H, J=6.6 Hz).

Provenance & Evidence