Water → 1-(2-Aminophenyl)-4-chloro-1-butanone

Participants

Reaction Conditions

Reaction Steps

A mixture of BCl3 (59.2 g, 0.50 mole) in 1,2-dichloroethane is treated with 4-chlorobutyronitrile (62.5 g, 0.604 mole) over a 1 hour period at -8° to 0° C., stirred for 1 hour at 0° to 5° C., treated with aniline (45.1 g, 0.485 mole) over a 1 hour period at 2° to 9° C., stirred for 1 hour, and treated with AlCl3 (68.8 g, 0.515 mole) in a single portion at ambient temperatures. The reaction mixture is sparged with nitrogen at reflux temperature for about 17 hours. The heated and sparged reaction mixture is cooled to 35° C. and added to approximately a 2-fold volume of water (based upon initial reaction volume) and stirred for 0.5 hour at 33° to 35° C. The phases are separated and the aqueous phase is washed with 1,2-dichloroethane. The organic phases are combined and concentrated in vacuo to give a solution of the title product containing, 85.9 g of the desired o-aminophenyl ketone, 89.7% yield, identified by HPLC analysis.

Provenance & Evidence