Methyl iodide → 2-[2-(Dimethylamino)phenyl]propanoic acid

Participants

Reaction Conditions

Reaction Steps

A solution of 2-[2-dimethylaminophenyl]acetic acid (1.8 g) in dry tetrahydrofuran (10 cc) is added at 10° C. to a solution of lithium diisopropylamide (prepared by the action of a 1.6M solution (2.6 cc) of butyllithium in hexane on a solution of diisopropylamine (2.8 g) in dry tetrahydrofuran (30 cc) at 10° C.). The reaction mixture is stirred for 30 minutes at 20° C. and then for 30 minutes at 35° C. After cooling to 20° C., methyl iodide (0.63 cc) is added and the mixture is heated for 1 hour at 35° C. The mixture is cooled and diluted with water (20 cc) and ethyl acetate (100 cc). The aqueous phase is washed with ethyl acetate (100 cc), acidified to pH 5 with hydrochloric acid and extracted with ethyl acetate (2×100 cc). The organic phases are washed with water, dried over magnesium sulphate and concentrated to dryness under reduced pressure (2.7 kPa) to give (RS)-2-[2-dimethylaminophenyl]propionic acid in the form of a yellow oil.

Provenance & Evidence