Ammonium Chloride → 2-(1-Naphthalenyl)-6,7-methylenedioxyquinolin-4-one

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Into a suspension of 150 (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). Yield 52% from 150 as a grayish-white solid; mp>350° C.; ESI-MS (Positive mode): m/z 316 [M+H]+; 1H-NMR (DMSO-d6, 8): 6.08 (1H, s), 6.15 (2H, s), 7.03 (1H, s), 7.46 (1H, s), 7.56-7.63 (2H, m), 7.63-7.70 (2H, m), 7.83 (1H, d, J=7.6 Hz), 8.06 (1H, d, J=7.6 Hz), 8.11 (1H, d, J=7.6 Hz), 11.90 (1H, s). IR (KBr): 1653 (C═O) cm−1; Anal. Calcd for C20H13NO3: C, 76.18; H, 4.16; N, 4.44. Found: C, 75.60; H, 3.94; N, 4.29.

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