Dimedone → 4-(3-Chlorophenyl)-2,7,7-trimethyl-4,6,7,8-tetrahydro-5(1H)quinolone

Participants

Reaction Steps

A mixture of 4-(3-chlorophenyl)but-3-en-2-one (5.0 g), 5,5-dimethyl-1,3-cyclohexanedione (3.88 g), ammonium acetate (3.20 g) and ethanol (90 mL) was heated at reflux for ten hours. The reaction mixture was worked up as described in Example 8 and recrystallization from ethyl acetate-hexane yielded the title compound (4.7 g) as a light yellow solid, mp 183°-185° C.; NMR: 0.94(s,3, CH3), 1.00 (s,3, CH3), 1.74 (s,3, CH3), 1.95 (d,1, J=16, CH), 2.11 (d,1, J=16, CH), 2.25 (d,1, J=16.7, CH), 2.35 (d,1, J=16.7, CH), 4.38 (d,1, J=4.6, CH), 4.59 (d,1, J=4.6, CH), 7.09-7.28 (m,4, Ar), 8.44 (s,1, NH); (CI, CH4) MS: m/z=302(M+1). Analysis for C18H20ClNO: Calculated: C, 71.63; H, 6.68; N, 4.64; Found: C, 71.60; H, 6.69; N, 4.54.

Provenance & Evidence