Reacción #82706

Ecuación de reacción

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

1.3-cyclohexanedione

ammonium acetate

→

title compound

Rendimiento 34.0%

4-(4-Chlorophenyl)-2-methyl-4,6,7,8-tetrahydro-5(1H)-quinolone

Rendimiento 34.0%

Disolventes

ethanol

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturaheated
2. 2
   Temperaturaat reflux for 5.5 h
3. 3
   OtroThe solvent was evaporated
4. 4
   Extracciónextracted with ethyl acetate
5. 5
   LavadoThe combined organic extracts were washed (water, brine)
6. 6
   Otrodried
7. 7
   Otroevaporated
8. 8
   Otroto yield a residue which
9. 9
   Otrowas chromatographed
10. 10
    Lavadoeluting with hexane:ethyl acetate (1:1)

Procedimiento

4-(4-Chlorophenyl)-3-butene-2-one (2.83 g), 1.3-cyclohexanedione (1.81 g), and ammonium acetate (2.60 g) were combined in ethanol (125 mL) and heated at reflux for 5.5 h. The solvent was evaporated, and the residue was taken up in water and extracted with ethyl acetate. The combined organic extracts were washed (water, brine), dried, and evaporated to yield a residue which was chromatographed, eluting with hexane:ethyl acetate (1:1) to yield the title compound as a pale yellow solid (1.46 g); mp 184°-187° C.; MS: 273 (M); NMR: 1.73 (s,3, CH3), 1.75-1.98 (m,2, CH2), 2.15 (m,2, CH2), 2.43 (t,2, J=6.0, CH2), 4.39 (d,1, J=4.7, CH), 4.58 (d,1,J=4.8, CH), 7.14 (d,2, J=8.4, Ar), 7.26 (d,2, J=8.4, Ar), 8.48 (s,1, NH); Analysis for C16H16ClNO: Calculated: C, 70.20; H, 5.89; N, 5.12; Found: C, 70.21; H, 5.67; N, 5.02.

Fuente