反应详情

A suspension of the crude 1,3,4,9-tetrahydrocarbazole-2-one oxime (1.093 g, 5.45 mmol) in ethanol (27.5 mL) was treated while cooling in ice bath with 2.5 N aqueous sodium hydroxide (22 mL). To the stirred dark solution kept under nitrogen was added portionwise over 15 minutes Al—Ni alloy (2.05 g). After 5 minutes the cooling bath was removed and the mixture stirred at room temperature for one hour. The catalysts was filtered off over Celite, the cake quickly washed under nitrogen with a small amount of 1:1 (v/v) ethanol-water and the filtrate was extracted three times with dichloromethane. The combined extracts were washed with water and brine and dried over anhydrous magnesium sulfate. Removal of the solvent provided a dark brown foam that crystallized upon standing. The residue was purified by flash chromatography over silica gel Merck 60 using a gradient from 3% to 10% of ammonia saturated methanol in dichloromethane to provide the title amine as a foam (0.791 g). MS (ES): [M+H]+ @m/z 187.1

1. additionwas treated
2. customAfter 5 minutes the cooling bath was removed
3. filtrationThe catalysts was filtered off over Celite
4. washthe cake quickly washed under nitrogen with a small amount of 1:1 (v/v) ethanol-water
5. extractionthe filtrate was extracted three times with dichloromethane
6. washThe combined extracts were washed with water and brine
7. dry with materialdried over anhydrous magnesium sulfate
8. customRemoval of the solvent
9. customprovided a dark brown foam that
10. customcrystallized
11. customThe residue was purified by flash chromatography over silica gel Merck 60 using a gradient from 3% to 10% of ammonia saturated methanol in dichloromethane