Reacción #82737

Ecuación de reacción

3-carboethoxy-2-trifluoromethyl-2-hydroxy-4-(3-cyanophenyl)-4,6,7,8-tetrahydro-5 (1H)-quinolone

lithium hydroxide monohydrate

hydrochloric acid

→

3-carboxy-2-trifluoromethyl-2-hydroxy-4-(3-cyanophenyl)-4,6,7,8-tetrahydro-5 (1H)-quinolone

Rendimiento 84.6%

Disolventes

water

ethanol

water

Condiciones de reacción

Tratamiento posterior

1. 1
   Extracciónextracted with ethyl acetate
2. 2
   LavadoThe combined organic extracts were washed (water and brine)
3. 3
   Otrodried
4. 4
   Filtraciónfiltered
5. 5
   Otroevaporated
6. 6
   Otroto yield a foam which
7. 7
   Otrowas purified by chromatography (ethyl acetate and ethyl acetate/methanol, 3:1)

Procedimiento

A suspension of 3-carboethoxy-2-trifluoromethyl-2-hydroxy-4-(3-cyanophenyl)-4,6,7,8-tetrahydro-5 (1H)-quinolone (3.39 g) in ethanol (20 ml) and water (20 ml) was treated with lithium hydroxide monohydrate (0.75 g). The mixture was heated at 90° C. for 1.5 hours, diluted with water, acidified with 1N hydrochloric acid, and extracted with ethyl acetate. The combined organic extracts were washed (water and brine), dried, filtered, and evaporated to yield a foam which was purified by chromatography (ethyl acetate and ethyl acetate/methanol, 3:1) to afford 3-carboxy-2-trifluoromethyl-2-hydroxy-4-(3-cyanophenyl)-4,6,7,8-tetrahydro-5 (1H)-quinolone (2.67 g) as a pale yellow foam; MS: m/z =381(m).

Fuente