Acetic Acid → 4-[Amino(carboxy)methyl]-3-methylbenzoic acid

Participants

Reaction Steps

A stirred mixture of 5-(4-cyano-2-methylphenyl)hydantoin (1.1 g, 5.2 mmol) in aqueous sodium hydroxide (2M, 12 ml) was heated to 120° C. for 17 hours in a PTFE lined stainless steel sealed reaction vessel. The cooled mixture was acidified with glacial acetic acid (1.4 ml) and chromatographed on ion exchange (Dowex 50×8-100 resin). The column was eluted sequentially with water, tetrahydrofuran-water (1:1), water and 10% pyridine in water. Fractions collected from the pyridine-water elution were combined and evaporated to dryness, redissolved in water and freeze-dried to give the title compound as a white powder, m.p. >250° C.

Provenance & Evidence