反応 #4177

反応方程式

potassium hydroxide

ethylene glycol

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

dichloromethane

→

product

収率 32.0%

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

収率 32.0%

溶媒

water

water

反応条件

後処理

1. 1
   温度the reaction mixture was cooled to room temperature
2. 2
   その他The aqueous phase was separated
3. 3
   抽出extracted with two 250 ml-portions of dichloromethane
4. 4
   温度The aqueous phase was then cooled in an ice-bath
5. 5
   抽出The product was extracted out with three 500 ml-portions of dichloromethane
6. 6
   洗浄The combined organic extracts were washed twice with brine
7. 7
   その他dried
8. 8
   ろ過filtered
9. 9
   濃縮concentrated

実験手順

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.

出典