反应 #5463

反应方程式

sodium hydride

indole-3-carboxylic acid

sodium hydroxide

Dimethylsulfate

→

colorless crystals

收率 75.3%

1-Methyl-1H-indole-3-carboxylic acid

收率 75.3%

溶剂

N,N-dimethylformamide

反应条件

后处理

1. 1
   温度A cooled
2. 2
   温度cooled
3. 3
   过滤The suspension was filtered
4. 4
   洗涤the wet solid was washed with water
5. 5
   温度refluxed for 30 minutes
6. 6
   其他the methanol was removed in vacuo
7. 7
   萃取The aqueous solution was extracted with ether (50 mL)
8. 8
   过滤The suspension was filtered
9. 9
   洗涤the solid was washed with water
10. 10
    干燥dried exhaustively m vacuo in the presence of Drierite
11. 11
    其他Recrystallization from acetonitrile

实验过程

A cooled (0° C.) suspension of 60% sodium hydride-oil dispersion (0.96 g, 24 mmol) in anhydrous N,N-dimethylformamide (15 mL) under nitrogen was treated in portions with indole-3-carboxylic acid (1.62 g, 10 mmol), and the mixture was stirred at 45°±5° C. for 30 minutes. Dimethylsulfate (3.03 g, 24 mmol) was added, and the mixture was heated to 100° C. for 30 minutes, cooled, and added to ice water (100 mL). The suspension was filtered and the wet solid was washed with water and taken up in 50% aqueous methanol (40 mL). The mixture was treated with 50% aqueous sodium hydroxide (3.0 g, 37.5 mmol) and refluxed for 30 minutes, then the methanol was removed in vacuo and replaced with water. The aqueous solution was extracted with ether (50 mL), then acidified with 3N HCl to pH 3 (15 mL). The suspension was filtered and the solid was washed with water and dried exhaustively m vacuo in the presence of Drierite. Recrystallization from acetonitrile afforded 1.32 g (75%) of colorless crystals; mp 201°-202° C. (dec).

来源