Water → HCID 178503115, compound

Participants

Reaction Conditions

Reaction Steps

Sodium nitrite (77 mg, 1.109 mmol) was added portionwise to concentrated sulfuric acid (2 mL) at 0° C. The mixture was stirred at 45° C. until homogeneous, cooled to 0° C., and charged with a solution of 5-[2-methyl-4-(methylthio)phenyl]-2-pyrazinamine (190 mg, 0.821 mmol) in sulfuric acid (3 mL) at 0° C. The mixture was warmed to ambient temperature, stirred at ambient temperature for 15 min, then at 45° C. for 5 h. The mixture was cooled to ambient temperature, poured into water, and the pH was adjusted to ˜4 with 10N NaOH. The resulting precipitate was filtered, washed with water, and air-dried to give 100 mg (52%) of 5-[2-methyl-4-(methylthio)phenyl]-2-pyrazinol (and tautomers thereof) as a tan solid. 1H NMR (400 MHz, DMSO-d6): δ 12.61-12.37 (m, 1H), 8.08 (d, 1H, J=1.0 Hz), 7.72-7.45 (m, 1H), 7.30 (d, 1H, J=8.1 Hz), 7.22-7.06 (m, 2H), 2.48 (s, 3H), 2.30 (s, 3H); LRMS (ESI), m/z 233 (M+H).

Provenance & Evidence