Reacción #82709

Ecuación de reacción

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

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturawere heated
2. 2
   Temperaturaat reflux overnight
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 solid
9. 9
   OtroRecrystallization from ethanol

Procedimiento

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.

Fuente