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

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Reaction Steps

A solution of 5-methyl-1-(3-nitrophenyl)-1-hexen-3-one (2.52 g), 1,3-cyclohexanedione (1.22 g) and ammonium acetate (1.88 g) in ethanol (65 mL) was stirred at reflux for 7.5 hours. After removal of the solvent, the residue was chromatographed (ethyl acetate/hexane 2:1) to yield the title compound (1.51 g) as a yellow solid; mp 158°-160° C.; NMR: 0.81 (d,3, J=5.8, CH3), 0.86 (d,3, J=5.8, CH3), 1.77-1.97 (m,5, CH2, CH), 2.10-2.23 (m,2, CH2), 2.46 (m,2, CH2), 4.59(d,1,J=4.8, CH), 4.64 (d,1, J=5.8, CH), 7.53 (m,1, Ar), 7.65 (m, 1, Ar), 7.97 (m,2, Ar), 8.49 (s,1, NH); MS: m/z=326(M). Analysis for C19H22N2O3 : Calculated: C, 69.92; H, 6.79; N, 8.58; Found: C, 70.03; H, 6.81; N, 8.54.

Provenance & Evidence