2-Chloro-5-methoxy-3-methyl-4-nitropyridine 1-oxide → 2-Chloro-5-methoxy-3-methylpyridin-4-amine

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Reaction Conditions

Reaction Steps

Iron powder (700 mg, 12 mmol) was added to a solution of C3 (350 mg, 1.60 mmol) in acetic acid (8 mL), and the reaction mixture was heated at 100° C. for 1 hour, then cooled to room temperature. After filtration through Celite and thorough washing of the filter pad with ethyl acetate and methanol, the combined filtrates were concentrated in vacuo. The residue was diluted with saturated aqueous sodium bicarbonate solution and extracted with ethyl acetate. The combined organic layers were washed with water, washed with saturated aqueous sodium chloride solution, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. Silica gel chromatography (Gradient: 50% to 75% ethyl acetate in heptane) afforded the product as a white solid. Yield: 240 mg, 1.39 mmol, 87%. LCMS m/z 173.0 [M+H+]. 1H NMR (400 MHz, CDCl3) δ 7.65 (s, 1H), 4.38 (br s, 2H), 3.91 (s, 3H), 2.20 (s, 3H).

Provenance & Evidence