Ammonium Chloride → (2-Chloropyridin-3-yl)methanol

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Reaction Steps

To a 0° C. solution of 2-chloropyridine-3-carbaldehyde (2.0 g, 14.1 mmol) in anhydrous methanol (80 mL) was added sodium borohydride (550 mg, 14.5 mmol). The reaction mixture was stirred at room temperature for 3 hours. Saturated ammonium chloride solution (20 mL) was added. The resultant mixture was extracted with dichloromethane (3×20 mL). The organic extracts were combined, dried over MgSO4, filtered, evaporated, and dried in vacuo, affording (2-chloropyridin-3-yl)methanol (800 mg, 40% yield). The product was used without further purification.

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