反応 #82709

反応方程式

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

1,3-cyclohexanedione

ammonium acetate

ethanol

→

title compound

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

反応条件

後処理

1. 1
   温度were heated
2. 2
   温度at reflux overnight
3. 3
   その他The solvent was evaporated
4. 4
   その他the residue was partitioned between water and ethyl acetate
5. 5
   その他The organic layer was dried
6. 6
   ろ過filtered
7. 7
   その他evaporated
8. 8
   その他to obtain a yellow solid
9. 9
   その他Recrystallization from ethanol

実験手順

A mixture of 4-(4-chlorophenyl)-3-butene-2-one (5.0 g), 1,3-cyclohexanedione (3.24 g), ammonium acetate (3.20 g) and 90 mL of ethanol were heated at reflux overnight and then cooled to room temperature. The solvent was evaporated and the residue was partitioned between water and ethyl acetate. The organic layer was dried, filtered, and evaporated to obtain a yellow solid. Recrystallization from ethanol provided the title compound as a yellow solid (3.0 g); mp 201°-203° C.; NMR: 1.73 (s,3, CH3), 1.87-1.98 (m,2, CH2), 2.13-2.17 (m,2, CH2), 2.43-2.49 (m,2, CH2), 4.40 (d,1, J=4.9, CH), 4.60 (d,1, J=4.9, CH), 7.09-7.25 (m,4, Ar), 8.50 (s,1, NH); (CI, CH4) MS: m/z=274(M+1). Analysis for C16H16ClNO.0.15 H2O: Calculated: C, 69.51; H, 5.94; N, 5.07; Found: C, 69.47; H, 6.03; N, 4.91.

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