反应详情

3,4-Dihydro-4-methylcyclopent[b]indol-1(2H)-one (1.7 g) and hydroxylamine hydrochloride (1.925 g) in pyridine were heated at 60° for 18h and cooled. The reaction mixture was evaporated in vacuo to a residue to which was added 8% sodium bicarbonate (150 ml). Extraction with ethyl acetate (300 ml) produced a suspension in the organic layer; this layer and associated solid was separated from the aqueous layer. The aqueous layer was re-extracted with ethyl acetate (250 ml). The combined organic extracts (and suspended solid) were evaporated to a residue, boiled with a mixture of ethanol (150 ml) and methanol (150 ml) and cooled to ca. 50°. The residue was adsorbed from this solution on to FCC silica and applied to an FCC column. Elution with ethyl acetate/3-10% methanol provided the title compound (1.69 g), m.p. 219°-224° (decomp.).

1. temperaturecooled
2. customThe reaction mixture was evaporated in vacuo to a residue to which
3. additionwas added 8% sodium bicarbonate (150 ml)
4. extractionExtraction with ethyl acetate (300 ml)
5. customproduced a suspension in the organic layer
6. customthis layer and associated solid was separated from the aqueous layer
7. extractionThe aqueous layer was re-extracted with ethyl acetate (250 ml)
8. customThe combined organic extracts (and suspended solid) were evaporated to a residue
9. additionboiled with a mixture of ethanol (150 ml) and methanol (150 ml)
10. temperaturecooled to ca. 50°
11. washElution with ethyl acetate/3-10% methanol