反应详情

A suspension of 3-carboxy-2-trifluoromethyl-2-hydroxy-4-(3-cyanophenyl)-4,6,7,8-tetrahydro-5(1H)-quinolone (2.25 g) in toluene (100 ml) was treated with p-toluene sulfonic acid monohydrate (0.33 g). The mixture was vigorously refluxed under Dean-Stark conditions for 1.5 hours and then partitioned between water and ethyl acetate. The organic portion was washed (water and brine) and evaporated. The residue was purified by chromatography (hexane/ethyl acetate, 1:1) to yield the title compound (1.04 g) as a white solid; m.p. 182°-183° C.; NMR: 1.80-2.00(m,2, CH2), 2.13-2.30(m,2,CH2), 2.50-2.67(m,2,CH2 4.68(d,1, CH, J=5.2), 5.61(d,1, CH, J=5.3), 7.51(m,2, Ar), 7.60(s,1, Ar), 7.64(m,1, Ar), 9.42(s,1, NH); MS: m/z =318(M); Analysis for C17H13F3N2O: Calculated: C, 64.15; H, 4.12; N, 8.80; Found: C, 64.15; H, 4.10; N, 8.63.

1. temperatureThe mixture was vigorously refluxed under Dean-Stark conditions for 1.5 hours
2. custompartitioned between water and ethyl acetate
3. washThe organic portion was washed (water and brine)
4. customevaporated
5. customThe residue was purified by chromatography (hexane/ethyl acetate, 1:1)