反应详情

A solution of 0.458 g of 9-benzyl-5-methoxy-8-fluoro-1,2,3,4-tetrahydrocarbazole-4-carboxamide in 13 ml of dry dioxane under nitrogen was treated with 0.59 g of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone and refluxed for one hour. The reaction mixture was cooled and filtered and the precipitate was washed with 15 ml of dioxane. The filtrate and washing were poured into saturated sodium bicarbonate solution and extracted three times with ethyl acetate. The extracts were washed with saturated sodium bicarbonate, with water and then with brine; dried over magnesium sulfate and concentrated. This residue was chromatographed on silica gel using dichloromethane/0-2% methanol to afford 0.45 g of subtitle compound. ESIMS m/e 349 (M++1)

1. temperaturerefluxed for one hour
2. temperatureThe reaction mixture was cooled
3. filtrationfiltered
4. washthe precipitate was washed with 15 ml of dioxane
5. washThe filtrate and washing
6. additionwere poured into saturated sodium bicarbonate solution
7. extractionextracted three times with ethyl acetate
8. washThe extracts were washed with saturated sodium bicarbonate, with water
9. dry with materialdried over magnesium sulfate
10. concentrationconcentrated
11. customThis residue was chromatographed on silica gel