Aluminum(III) Chloride → 6-bromo-4,4-dimethyl-3,4-dihydroquinolin-2(1H)-one

Participants

Reaction Conditions

Reaction Steps

To 1.0 g (3.9 mmol) of (4-bromophenyl) 3,3-dimethylacryloylamide heated to 130 degrees C. was added 0.526 g (3.94 mmol) of aluminum chloride over a period of 30 minutes. The reaction mixture was heated for an additional 30 minutes. The mixture was treated again with 0.079 g (0.592 mmol) of aluminum chloride and heated at 130 degrees C. for 1 hour and 40 minutes. The reaction mixture was extracted with 20 ml ether and the combined organics washed with 20 ml water, 20 ml brine and dried (MgSO4). Solvent was removed in-vacuo and the residue purified by flash chromatography (SiO2 ; 20% ethyl acetate in hexanes) to give the title compound as a light yellow solid.

Provenance & Evidence