Sodium borohydride → 6-Hydroxymethyl-3-(3-methylisoxazol-5-yl)-4-phenyl-1H-quinolin-2-one

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A mixture of 3-(3-methyl-isoxazol-5-yl)-2-oxo-4-phenyl-1,2-dihydro-quinoline-6-carboxaldehyde (a) (33 mg, 0.11 mmol), sodium borohydride (NaBH4) (4 mg, 0.1 mmol) in DCM (1 mL) and methanol (1 mL) was stirred at room temperature for 1.5 h, and then concentrated. To the residue was added DCM (10 mL) and water (1 mL). The organic layer was separated from the aqueous layer, dried (MgSO4), filtered, and concentrated. The residue was purified by flash chromatography on silica gel to give 6-hydroxymethyl-3-(3-methylisoxazol-5-yl)-4-phenyl-1H-quinolin-2-one (c) (33 mg, 90%). 1H NMR (300 MHz, CD3OD) δ 7.65-7.58 (m, 1H), 7.49-7.38 (m, 4H), 7.30-7.20 (m, 3H), 6.30 (s, 1H), 4.51 (s, 2H), 2.17 (s, 3H). MS: 333.2 (M+H).

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