反応 #82710

反応方程式

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

1,3-cyclohexanedione

ammonium acetate

ethanol

→

title compound

収率 25.3%

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

収率 25.3%

溶媒

ether

hexane ethyl acetate

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 an amber oil

実験手順

A mixture of 4-(4-methyphenyl)-3-butene-2-one (5.0 g), 1,3-cyclohexanedione (3.66 g), ammonium acetate (3.61 g) and 100 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 an amber oil. Chromatography, with hexane:ethyl acetate (1:1) as the eluent, and trituration from ether provided the title compound as an off-white solid (2.0 g); mp 196°-198° C.; NMR: 1.73 (s,3, CH3), 1.87-1.98 (m,2, CH2), 2.14-2.16 (m,2, CH2), 2.22 (s,3, CH3), 2.43-2.49 (m,2, CH2) 4.34 (d,1, CH), 4.57 (d,1, CH), 7.01 (s,4, Ar), 8.40 (s,1, NH); (CI, CH4) MS: m/z=254(M+1). Analysis for C17H19NO: Calculated: C, 80.60; H, 7.56; N, 5.53; Found: C, 80.24; H, 7.68; N, 5.36.

出典