反应详情

温度

100 °C

A mixture of methyl 3-formyl-1H-indole-6-carboxylate (12.0 g), p-toluenesulphonic acid (2.0 g) and p-toluenesulphonylhydrazide (13.0 g) in a mixture of dimethylformamide (100 ml) and sulpholane (50 ml) was heated at 100° C. for 15 minutes and then cooled to room temperature. The mixture was treated with sodium cyanoborohydride (15.0 g, 5 g portions after 10 minute intervals), then heated at 100° C. for 2 hours. After cooling to ambient temperature the reaction mixture was treated with ice water (500 ml) giving a white precipitate. Water (1000 ml) was added and the mixture stirred for 30 minutes then filtered. The off-white solid was washed with warm water then azeotroped with toluene to yield the title compound (10.2 g) as a white solid.

1. temperaturecooled to room temperature
2. temperatureheated at 100° C. for 2 hours
3. temperatureAfter cooling to ambient temperature the reaction mixture
4. customgiving a white precipitate
5. filtrationthen filtered
6. washThe off-white solid was washed with warm water
7. customthen azeotroped with toluene