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-Tetrahydro-1H-benz[cd]indol-2-one (3.0 g, 17 mmol) was dissolved in anhydrous N,N-dimethylformamide (120 ml), and the solution was mixed with sodium hydride (60%, 760 mg, 190 mmol) and stirred at 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 removed by evaporation under a reduced pressure, and ethyl acetate, water and hydrochloric acid (1 N) were added to the resulting residue. The reaction product was extracted with ethyl acetate, washed with saturated brine and dried with anhydrous sodium sulfate, the solvent was removed by evaporation under a reduced pressure, and then the thus obtained material was separated and purified by a silica gel column chromatography to obtain 1.8 g (5.8 mmol, 33% in yield) of the title compound.

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