反応 #82707

反応方程式

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

1,3-cyclohexanedione

ammonium acetate

→

title compound

収率 39.8%

2-Methyl-4-(3-trifluoromethylphenyl)-4,6,7,8-tetrahydro-5(1H)-quinolone

収率 39.8%

溶媒

ethanol

反応条件

後処理

1. 1
   温度were heated
2. 2
   温度at reflux for eight hours
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 yield a yellow solid
9. 9
   その他Recrystallization from ethyl acetate

実験手順

A mixture of 4-(3-trifluoromethylphenyl)-3-butene-2-one (4.9 g), 1,3-cyclohexanedione (2.68 g), ammonium acetate (2.65 g) and 75 mL of ethanol were heated at reflux for eight hours 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 yield a yellow solid. Recrystallization from ethyl acetate provided the title compound (2.8 g) as an off-white solid; mp 184°-185° C.; NMR: 1.74 (s,3, CH3), 1.87-1.98 (m,2, CH2), 2.13-2.19 (m,2, CH2), 2.42-2.49 (m,2, CH2), 4.50 (d,1, J=4.9, CH), 4.63 (d,1, J=4.9, CH), 7.45 (s,4, Ar), 8.53 (s,1, NH); (CI, CH4) MS: m/z=308(M+1). Analysis for C17H16F3NO: Calculated: C, 66.44; H, 5.25; N, 4.56; Found: C, 65.90; H, 5.33; N, 4.43.

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