To a stirred solution of 2,6-dichloropyridine (68.9 g, 466 mmol) in methanol (500 mL) was slowly added sodium methanolate (100 g, 1.86 mol) at room temperature. The reaction mixture was stirred continuously at 60°C for 24 hours. After completion of the reaction, the mixture was cooled to room temperature, the reaction was quenched with 2 M aqueous hydrochloric acid and extracted with dichloromethane (CH2Cl2). The organic layers were combined, dried with anhydrous magnesium sulfate (MgSO4), filtered and concentrated under reduced pressure to afford 2-chloro-6-methoxypyridine (66.9 g, quantitative yield) as a colorless oil. The product characterization data were as follows: IR (thin film method, cm?1 ): 1599, 1585, 1560, 1468, 1410, 1302, 1265, 1152, 1024, 876, 789; 1H-NMR (CDCl3, 500 MHz) δ: 7.51 (t, J = 7.37 Hz, 1H), 6.90 (d, J = 7.37 Hz, 1H), 6.65 (d, J = 7.37 Hz, 1H), 3.94 (s, 3H); 13C-NMR (CDCl3, 125 MHz) δ: 163.9, 148.4, 140.5, 116.2, 109.1, 54.0; HR-MS (ESI-TOF): the calculated C6H7ClNO [(M + H)+] value was 144.0211 and the measured value was 144.0211.
