Reacción #82707

Ecuación de reacción

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

1,3-cyclohexanedione

ammonium acetate

→

title compound

Rendimiento 39.8%

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

Rendimiento 39.8%

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 yield a yellow solid
9. 9
   OtroRecrystallization from ethyl acetate

Procedimiento

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.

Fuente