Dimethyl Sulfoxide → 5-(4-Carboxyphenyl)-2-hydroxypyridine

Participants

Reaction Conditions

Reaction Steps

4-(6-Methoxypyridin-3-yl)benzoic acid (3.34 g, 14.6 mmol), dimethylsulfoxide (6 mL), and pyridinium hydrochloride (8.43 g, 72.9 mmol) were heated together, with stirring, at 160° C. for 15 minutes. The reaction mixture was cooled to ˜90° C., and water added slowly (100 mL). The solution/suspension was cooled to 0° C., the precipitate filtered off and washed with water. The wet product was dried by azeotroping off the residual water with methanol to give the product as a white solid (2.38 g, 11.1 mmol). 1H NMR (DMSO) δ 7.93 (d, 2H), 7.91-7.78 (m, 2H), 7.68 (d, 2H), 6.43 (d, 1H). ESI MS (M+1)+: 216.

Provenance & Evidence