Hydrochloric Acid → 4-Hydroxy-1-methyl-3-nitropyridin-2(1H)-one

Participants

Reaction Conditions

Reaction Steps

To 4-hydroxy-3-nitro-1H-pyridin-2-one (300 mg, 1.9 mmol) in DMF (5 mL) was added NaH (176 mg, 4.4 mmol, 60% in mineral oil) at 0° C. under N2. After stirring at 0° C. for 30 min, CH3I (272 mg, 1.9 mmol) in DMF (5 mL) was added dropwise, and the mixture was stirred for 2 h at 25° C. Saturated aqueous NH4Cl was added, the pH was adjusted to −3 with 1N HCl and EA extractive work up gave a residue that was triturated with MeOH (0.5 ml):EA (10 mL):PE (5 mL). After filtration, the trituratate was evaporated to give the title compound (300 mg, 91%) as a yellow solid. 1H NMR: (CDCl3, 400 MHz) δ: 7.75 (d, J=7.2 Hz, 1H), 6.17 (d, J=7.2 Hz, 1H) 3.54 (s, 3H). LCMS: 171.0 (M+1)+

Provenance & Evidence