Реакция #4177

Уравнение реакции

potassium hydroxide

ethylene glycol

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

dichloromethane

→

product

Выход 32.0%

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

Выход 32.0%

Растворители

water

water

Условия реакции

Обработка

1. 1
   Температураthe reaction mixture was cooled to room temperature
2. 2
   ДругоеThe aqueous phase was separated
3. 3
   Экстракцияextracted with two 250 ml-portions of dichloromethane
4. 4
   ТемператураThe aqueous phase was then cooled in an ice-bath
5. 5
   ЭкстракцияThe product was extracted out with three 500 ml-portions of dichloromethane
6. 6
   ПромывкаThe combined organic extracts were washed twice with brine
7. 7
   Другоеdried
8. 8
   Фильтрацияfiltered
9. 9
   Концентрированиеconcentrated

Методика

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.

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