N-ethyl carbazole → 3,6-Bis(4-chlorobutyryl)-N-ethylcarbazole

Participants

Reaction Steps

To a solution of 78.0g (0.4 mole) of N-ethylcarbazole and 141 g (1.0 mole) of 4-chlorobutyrylchloride in 1 l of methylene chloride, previously cooled to 0°C, 127.0 g (0.95 mole) of aluminum chloride was added portionwise. The mixture was stirred at room temperature for 16 hours, and the resulting complex was decomposed with concentrated HCl/ice. The organic layer was separated, washed with water, dried over magnesium sulfate and treated with pentane to precipitate the desired product which was recrystallized from acetone and then acetone-methanol. M.P. 106°-108°C, λmaxEtOH 259, E1cm1% 1030.

Provenance & Evidence