Nitric Acid → 5-Bromo-2-methyl-4-nitropyridine 1-oxide

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-bromo-2-methylpyridine N-oxide (660 mg, 3.51 mmol) in sulfuric acid (1.6 mL) at 0° C. was added a premixed solution of nitric acid (1.5 mL) in sulfuric acid (2.5 mL). The resulting reaction was warmed to 25° C. then heated to 80° C. After 12 h, the solution was poured into ice then, neutralized with 6N NaOH and extracted several times with DCM. The combined organic fractions were dried over Na2SO4, concentrated and purified via column chromatography (silica, 1% MeOH in DCM) yielding the title compound (558 mg, 81%) as a yellow solid: LCMS (ES) m/z=235 (M+H)+.

Provenance & Evidence