Aniline → alpha-(Phenylamino)benzeneacetic acid

Participants

Reaction Steps

α-Bromophenylacetic acid (5.01 g, 23.2 mmol.) is dissolved in aniline (25 mL, 274 mmol) and the mixture reacted in a closed vessel under MW irradiation at 120° C. for 5 minutes (LC-MS monitoring: complete conversion). Dichloromethane (DCM) (100 mL) is added to the reaction mixture and the resulting solid is filtered; 2M Na2CO3 (50 mL) is added to the solution, and the aqueous layer is washed with DCM (3×100 mL). The aqueous layer is acidified with 12N HCl (36 mL), and the title compound is recovered as racemic mixture by filtration (5.1 g, 97% yield, white solid).

Provenance & Evidence