1,3-Cyclohexanedione → 2-(t-Butyl)-4-(3-nitrophenyl)-4,6,7,8-tetrahydro-5(1H)-quinolone

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Reaction Steps

t-Butyl-3-nitrostyrylketone (1.81 g), 1.3-cyclohexanedione (0.82 g), and ammonium acetate (1.25 g) were combined in ethanol (50 mL) and heated at reflux for 7.5 hours. Following removal of solvent and chromatography (hexane/ethyl acetate; 1:1 and methylene chloride/acetonitrile 9:1) the title compound (0.54 g) was obtained as a yellow solid; mp 180°-181.5° C.; NMR: 1.12 (s,9, CH3), 1.68-1.95 (m,2, CH2), 2.06-2.27 (m,2, CH2), 2.42-2.67 (m,2, CH2), 4.61 (d,1, J=5.2 CH), 4.72 (dd,1, J=5.2, 1.8; CH), 7.53 (m,1, Ar), 7.64 (m,1, Ar), 7.97 (m,2, Ar), 8.10 (s,1, NH); MS: m/z=326(M). Analysis for C19H22N2O3: Calculated: C, 69.92; H, 6.79; N, 8.58; Found: C, 69.96; H, 6.80; N, 8.60.

Provenance & Evidence