1,4-Dibromobutane → 2a-(4-Bromobutyl)-2a,3,4,5-tetrahydrobenz[cd]indole-2(1H)-one

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Reaction Steps

2a, 3,4,5-Tetrahydrobenz [cd]indole-2(1H) -one (3.0 g, 17 mmol) was dissolved in anhydrous N,N-dimethylformamide (120 ml). Thereto was added an oily sodium hydride (760 mg, 19 mmol), and the resulting solution was stirred at a room temperature for 1 hour. The reaction solution was mixed with 1,4-dibromobutane (6.3 ml, 52 mmol) and again stirred for 17 hours. The solvent was evaporated under a reduced pressure, and the thus obtained residue was mixed with ethyl acetate, water and hydrochloric acid (1 N). The reaction product was extracted with ethyl acetate, washed with saturated brine and dried with anhydrous sodium sulfate. Then the compound obtained by the evaporation of the solvent under a reduced pressure was separated and purified by a silica gel column chromatography to obtain 1.8 g of the title compound (5.8 mmol, 33% in yield).

Provenance & Evidence