1,3-Cyclohexanedione → HCID 19381235, compound

Participants

Reaction Steps

A mixture of 1-(3-nitrophenyl)-1-penten-3-one (2.42 g), 1,3-cyclohexanedione (1.36 g), ammonium acetate (2.00 g) and ethanol (70 mL) was heated at reflux for 7.5 hours. Removal of solvent, chromatography (ethyl acetate/hexane, 2:1 and methylene chloride/acetonitrile, 9:1), trituration with hot diethyl ether and recrystallization from ethyl acetate provided the title compound (1.29 g) as a yellow solid; mp 182°-184° C.; NMR: 1.03 (t,3, J=7.4, CH3), 1.70-1.95 (m,2, CH2), 2.07 (q,2, J=7.5, CH2), 2.17 (m,2, CH2), 2.48 (m,2, CH2), 4.59 (d,1, J=4.8, CH), 4.66 (dd, 1, J=4.8, 0.9, CH), 7.53 (m,1, Ar), 7.64 (m,1, Ar), 7.98 (m,2, Ar), 8.55 (s,1, NH). MS: m/z= 298(M). Analysis for C17H18N2O3 : Calculated: C., 68.44; H, 6.08; N, 9.39; Found: C, 68.43; H, 6.09; N, 9.39.

Provenance & Evidence