反应详情

A mixture of 1-(3,4-dichlorophenyl)but-1-en-3-one (5.0 g), 1,3-cyclohexanedione (2.71 g), ammonium acetate (2.70 g) and ethanol (75 mL) was heated at reflux for ten hours. The reaction was worked up as described in Example 8, and recrystallization from ethyl acetate-hexane yielded the title compound (2.6 g) as an off-white solid, mp 199°-201° C.; NMR: 1.74 (s,3, CH3), 1.84-1.88 (m,2, CH2), 2.14-2.19 (m,2, CH2), 2.41-2.46 (m,2, CH2), 4.42 (d,1, J=4.7, CH), 4.59 (d,1, J=4.7, CH), 7.12 (dd,1, J=8.3,2.0, Ar), 7.31 (d,1, J=2.0, Ar), 7.48 (d,1, J=8.3, Ar), 8.55 (s,1, NH); (CI, CH4) MS: m/z=308(M+1). Analysis for C16H15C12NO: Calculated: C, 62.35; H, 4.91; N, 4.54; Found: C, 62.03; H, 5.09; N, 4.44.

1. temperaturewas heated
2. temperatureat reflux for ten hours
3. customas described in Example 8, and recrystallization from ethyl acetate-hexane