(2) Synthesis of 2-chloro-3-methoxy-6-methylpyridine: 2-chloro-6-methylpyridin-3-ol (5.1 g, 35.4 mmol) was dissolved in 40 mL of acetone and solid sodium carbonate (6.62 g, 53.1 mmol) was added. Iodomethane (9.07 g, 70.8 mmol) was slowly added dropwise to the reaction mixture under stirring at 50 °C for 5 h with continuous stirring. After completion of the reaction, acetone was removed by distillation under reduced pressure and the residue was purified by silica gel column chromatography to afford the target product 2-chloro-3-methoxy-6-methylpyridine as a white solid. Yield: 4.53 g, yield: 81.3%, melting point: 43-45 °C. IR (KBr, cm-1): 1572, 1473, 1302, 1101, 1020, 825, 747. 1H-NMR (60 MHz, CDCl3, δ): 2.4 (3H, s, CH3), 3.8 (3H, s, OCH3), 6.9 ( 1H, d, J=8Hz, pyridine ring H), 7.05 (1H, d, J=8Hz, pyridine ring H).
