Thionyl Chloride → Methyl 3-aminophenylacetate

Participants

Reaction Steps

Methanol (20 mL) was cooled to −10 degrees under an atmosphere of argon. To the solvent was added dropwise thionyl chloride (4.31 mL) and a solution of 3-aminophenylacetic acid (3.00 g) in methanol (25 mL) and the mixture was stirred at −10˜0 degrees for 1 hour. To the reaction mixture was added saturated aqueous solution of sodium bicarbonate and the mixture was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium chloride, dried over sodium sulfate, and then concentrated. The residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:1) to give the title compound (3.90 g) having the following physical data.

Provenance & Evidence