Ethyl Acetate → 1-(2-Aminophenyl)-2-methylpropan-1-one

Participants

Reaction Steps

A solution of anthranilonitrile (8.507 gm, 72 mmol) in dry Et2O (20 ml) was added to i-propylmagnesium chloride (2.0M in Et2O, 100 ml, 200 mmol) in dry Et2O (30 ml) at 0° C. over a 15 minute period. After the addition was complete, the mixture was warmed to room temperature and stirred for 4.5 hours. The solution was cooled to 0° C., quenched with 10% HCl (150 ml), then stirred for 25 minutes. The aqueous layer was made basic with solid NaOH (25 gm) and then extracted with Et2O (3×). The combined Et2O extracts were washed with brine, then dried (Na2SO4), filtered and stripped to give a yellow oil. Flash Chromatography of the oil (Merck SiO2, 15% EtOAc in hexane) afforded 1-(2-aminophenyl)-2-methyl-1-propanone (10.916 gm, 93%) as a golden yellow oil.

Provenance & Evidence