11B. 6-Chloropyridin-3-yl acetate (11.1 g, 64.7 mmol) from step 11a was dissolved in methanol at room temperature, followed by addition of solid potassium carbonate (4.47 g, 32.4 mmol). The reaction mixture was stirred for 2 hours and the volatiles were removed under reduced pressure. The residue was diluted with ether and water, and the aqueous phase was neutralized to pH 7 by addition of aqueous 1 N hydrochloric acid.The organic and aqueous layers were separated and the aqueous phase was extracted twice with ether. The organic extracts were combined, dried over magnesium sulfate and concentrated to give 2-chloro-5-hydroxypyridine as a white solid (8.03 g, 96% yield): melting point 155 °C; 1H NMR (CD3OD, 300 MHz) δ 7.20-7.28 (m, 2H), 7.88 (m, 1H); mass spectrum (CI/NH3) m/z: 130,132 (M+H) +; 147,149 (M+NH4)+.
