反応 #82706

反応方程式

4-(4-Chlorophenyl)-3-butene-2-one

1.3-cyclohexanedione

ammonium acetate

→

title compound

収率 34.0%

4-(4-Chlorophenyl)-2-methyl-4,6,7,8-tetrahydro-5(1H)-quinolone

収率 34.0%

溶媒

ethanol

反応条件

後処理

1. 1
   温度heated
2. 2
   温度at reflux for 5.5 h
3. 3
   その他The solvent was evaporated
4. 4
   抽出extracted with ethyl acetate
5. 5
   洗浄The combined organic extracts were washed (water, brine)
6. 6
   その他dried
7. 7
   その他evaporated
8. 8
   その他to yield a residue which
9. 9
   その他was chromatographed
10. 10
    洗浄eluting with hexane:ethyl acetate (1:1)

実験手順

4-(4-Chlorophenyl)-3-butene-2-one (2.83 g), 1.3-cyclohexanedione (1.81 g), and ammonium acetate (2.60 g) were combined in ethanol (125 mL) and heated at reflux for 5.5 h. The solvent was evaporated, and the residue was taken up in water and extracted with ethyl acetate. The combined organic extracts were washed (water, brine), dried, and evaporated to yield a residue which was chromatographed, eluting with hexane:ethyl acetate (1:1) to yield the title compound as a pale yellow solid (1.46 g); mp 184°-187° C.; MS: 273 (M); NMR: 1.73 (s,3, CH3), 1.75-1.98 (m,2, CH2), 2.15 (m,2, CH2), 2.43 (t,2, J=6.0, CH2), 4.39 (d,1, J=4.7, CH), 4.58 (d,1,J=4.8, CH), 7.14 (d,2, J=8.4, Ar), 7.26 (d,2, J=8.4, Ar), 8.48 (s,1, NH); Analysis for C16H16ClNO: Calculated: C, 70.20; H, 5.89; N, 5.12; Found: C, 70.21; H, 5.67; N, 5.02.

出典