Ammonium Chloride → 2-(3-Benzo[b]furyl)-6,7-methylenedioxyquinolin-4-one

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Into a suspension of 155 (2.95 mmol) in t-butyl alcohol (100 mL) was added potassium t-butoxide (1.66 g, 14.7 mmol). The mixture was refluxed under argon for 12 h, cooled, and poured into a 10% ammonium chloride solution (100 mL). The solid precipitate was collected and washed with EtOH. The crude product was purified by flash chromatography (silica gel, CH2Cl2: EtOH 16:1-10:1). Obtained as a pale-yellow solid from 155; yield 17%; mp>315° C.; ESI-MS (Positive mode): m/z 306 [M+H]+; 1H-NMR (400 MHz, DMSO-d6): δ 6.12 (2H, s), 6.49 (1H, s), 7.13 (1H, s), 7.36-7.45 (3H, m), 7.69 (1H, d, J=8.0 Hz), 8.14 (1H, s), 8.52 (1H, s); IR (KBr): 1626 (C═O) cm−1; Anal. Calcd for C18H11NO4: C, 70.82; H, 3.63; N, 4.59. Found: C, 70.52; H, 3.95; N, 4.21.

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