Reacción #4119

Ecuación de reacción

potassium hydroxide

ethylene glycol

2-(5-methyl-7-nitroindolin-1-yl)benzonitrile

dichloromethane

→

product

Rendimiento 32.0%

2-(5-Methyl-7-nitro-1-indolinyl)benzoic acid

Rendimiento 32.0%

Disolventes

water

water

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturathe reaction mixture was cooled to room temperature
2. 2
   OtroThe aqueous phase was separated
3. 3
   Extracciónextracted with two 250 ml-portions of dichloromethane
4. 4
   TemperaturaThe aqueous phase was then cooled in an ice-bath
5. 5
   ExtracciónThe product was extracted out with three 500 ml-portions of dichloromethane
6. 6
   LavadoThe combined organic extracts were washed twice with brine
7. 7
   Otrodried
8. 8
   Filtraciónfiltered
9. 9
   Concentraciónconcentrated

Procedimiento

A stirred solution under nitrogen of potassium hydroxide (30 g, 0.53 mole) in ethylene glycol (250 ml) and water (35 ml) was heated to 175° C., at which temperature there was added 2-(5-methyl-7-nitroindolin-1-yl)benzonitrile (26 g, 0.093 mole). After heating at 175° C. for 3 hours, the reaction mixture was cooled to room temperature and dichloromethane (1 liter) and water (500 ml), were added, with stirring. The aqueous phase was separated and extracted with two 250 ml-portions of dichloromethane. The aqueous phase was then cooled in an ice-bath and acidified with concentrated hydrochloric acid. The product was extracted out with three 500 ml-portions of dichloromethane. The combined organic extracts were washed twice with brine, dried, filtered, and concentrated to afford 9.0 g (32%) of product.

Fuente