Acetic Acid → 1-(2-propynyl)benz[cd]indol-2(1H)-one

Participants

Reaction Steps

Potassium-t-butoxide, 6.17 g (0.055 mol) was added to a solution of 8.46 g (5 mmol) of benz[cd]indol-2(1H)-one in 100 ml of dimethylformamide. After stirring for 10 minutes at room temperature, 4.9 ml (0.055 mol) of propargyl bromide was added and the mixture was stirred for 1 hour at room temperature. The reaction mixture was acidified with acetic acid and partitioned between methylene chloride and saturated aqueous sodium bicarbonate solution. The organic layer was dried and evaporated and the residue was crystallized from tetrahydrofuran/ethanol to leave 8 g (77%) of product with m.p. 183°-186° C. The title compound was recrystallized for analysis twice from methylene chloride/ethyl acetate and had m.p. 185°-187° C.

Provenance & Evidence