To a stirred solution of methanol (15 mL) was added potassium carbonate (1.10 g, 0.0081 mol) as 6-chloro-5-methylpyridin-3-yl acetate (750 mg, 0.004 mol) at room temperature. The reaction mixture was stirred continuously at ambient temperature for 1 hour. Subsequently, the solvent was removed by concentration under reduced pressure and the residue was diluted with a minimal amount of water and neutralized with 1N hydrochloric acid (15 mL). After neutralization was complete, the solution was extracted using ethyl acetate (2 x 100 mL). The combined organic layers were washed with brine, dried over anhydrous sodium sulfate and concentrated to give 6-chloro-5-methylpyridin-3-ol as an off-white solid (500 mg, 89% yield). Mass spectrometry analysis showed m/z = 143.01 [M + H]+. 1H-NMR (300 MHz, DMSO-d6) data were as follows: δ 10.09 (s, 1H), 7.76 (d, J = 3Hz, 1H), 7.18 (d, J = 3.6Hz, 1H), 2.24 (s, 3H).
