反応 #5463
ord-042aee9b85f3448db5bd4bc2f82e203c
反応方程式
反応条件
後処理
- 1温度A cooled
- 2温度cooled
- 3ろ過The suspension was filtered
- 4洗浄the wet solid was washed with water
- 5温度refluxed for 30 minutes
- 6その他the methanol was removed in vacuo
- 7抽出The aqueous solution was extracted with ether (50 mL)
- 8ろ過The suspension was filtered
- 9洗浄the solid was washed with water
- 10乾燥dried exhaustively m vacuo in the presence of Drierite
- 11その他Recrystallization from acetonitrile
実験手順
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).