51269-81-9

22620-34-4

General procedure for the synthesis of 5-chloro-3-pyridinemethanol from 5-chloronicotinic acid methyl ester: Sodium borohydride (16.4 g, 434 mmol) was slowly added to a mixed solution of 5-chloronicotinic acid methyl ester (17.2 g, 101 mmol) in methanol (230 mL) and dichloromethane (230 mL) at 0 °C. The reaction mixture was stirred continuously for 18 hours at room temperature. Upon completion of the reaction, the mixture was concentrated under reduced pressure and subsequently diluted with deionized water (300 mL) and extracted with ethyl acetate (3 x 300 mL). The organic layers were combined, dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to afford the target product 5-chloro-3-pyridinemethanol (7.8 g, 54% yield). The structure of the product was confirmed by 1H NMR (400 MHz, DMSO-d6): δ 8.45-8.52 (m, 2H), 7.83 (s, 1H), 5.45 (t, J = 5.8 Hz, 1H), 4.55 (t, J = 5.7 Hz, 2H). Mass spectral analysis showed m/z of 144.1 [M+H]+.