Reaktion #4119

Reaktionsgleichung

potassium hydroxide

ethylene glycol

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

dichloromethane

→

product

Ausbeute 32.0%

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

Ausbeute 32.0%

Lösungsmittel

water

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe reaction mixture was cooled to room temperature
2. 2
   SonstigeThe aqueous phase was separated
3. 3
   Extraktionextracted with two 250 ml-portions of dichloromethane
4. 4
   TemperaturThe aqueous phase was then cooled in an ice-bath
5. 5
   ExtraktionThe product was extracted out with three 500 ml-portions of dichloromethane
6. 6
   WaschenThe combined organic extracts were washed twice with brine
7. 7
   Sonstigedried
8. 8
   Filtrationfiltered
9. 9
   Einengenconcentrated

Vorschrift

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.

Quelle