Reacción #82708

Ecuación de reacción

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

1,3-cyclohexanedione

ammonium acetate

→

title compound

Rendimiento 56.9%

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

Rendimiento 56.9%

Disolventes

ethanol

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturawere heated
2. 2
   Temperaturaat reflux for eight hours
3. 3
   OtroThe solvent was evaporated
4. 4
   Otrothe residue was partitioned between water and ethyl acetate
5. 5
   OtroThe organic layer was dried
6. 6
   Filtraciónfiltered
7. 7
   Otroevaporated
8. 8
   Otroto obtain a yellow oil
9. 9
   OtroChromatography, with hexane:ethyl acetate (1:1) as the eluent, and recrystallization from toluene

Procedimiento

A mixture of 4-(4-trifluoromethyphenyl)-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 obtain a yellow oil. Chromatography, with hexane:ethyl acetate (1:1) as the eluent, and recrystallization from toluene:hexane provided the title compound as a yellow solid (4.0 g); mp 116°-118° C.; NMR: 1.73 (s,3, CH3), 1.87-1.98 (m,2, CH2), 2.14-2.16 (m,2, CH2), 2.45-2.49 (m,2, CH2), 4.49 (d, 1, J=4.9, CH), 4.60 (d,1, J=4.9, CH), 7.35 (d,2, J=8.0, Ar), 7.57 (d,2, J=8.0, Ar), 8.54 (s,1, NH); (CI, CH4) MS: m/z=308(M+1); Analysis for Ci7H16F3NO: Calculated: C, 66.44; H, 5.25; N, 4.56; Found: C, 66.72; H, 5.34; N, 4.41.

Fuente