2-Chloro-4-picoline

695-34-1

3678-62-4

a) Sodium nitrite (13.88 g, 200 mmol) was slowly added to a concentrated hydrochloric acid (200 mL) solution of 2-amino-4-methylpyridine (15.0 g, 139 mmol) at 0 °C. The reaction mixture was gradually warmed to room temperature and stirred continuously for 16 hours. Upon completion of the reaction, the mixture was poured into ice (500 g). The pH of the mixture was adjusted using concentrated ammonia to 8.0. Subsequently, the mixture was extracted with ether (3 x 300 mL). The combined ether layers were washed sequentially with deionized water (2 × 200 mL) and saturated brine (200 mL). The organic layer was dried with anhydrous magnesium sulfate and concentrated under reduced pressure to give 2-chloro-4-methylpyridine (10.3 g, 58% yield) as a pale yellow oil. Mass spectrum (electrospray ionization) m/e 127.8 (M + H)+.