Ammonium Chloride → (5,7-Difluoroquinolin-6-yl)methanol

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Reaction Steps

To a solution of 5,7-difluoroquinoline-6-carbaldehyde (4.00 g, 20.71 mmol) in MeOH (120 mL), was added NaBH4 (0.79 g, 20.71 mmol) in portions. After stirring for 15 min, saturated aqueous solution of NH4Cl was added. The aqueous phase was extracted with CH2Cl2 (4×25 mL). The organic layers were combined and dried over NaSO4. The product was purified by silica gel with hexane:EtOAc to afford (5,7-difluoroquinolin-6-yl)methanol (3.80 g, 94%). NMR (400 MHz, CDCl3) δ ppm 8.97 (m, 1H), 8.42 (m, 1H), 7.63 (d, 1H), 7.46 (m, 1H), 4.99 (d, 2H), 2.07 (t, 1H). LCMS (method B): [MH]+=196.0, tR=1.67 min

Provenance & Evidence