Sodium Hydroxide → 3-Methoxy-4-o-tolylureidophenylacetic acid

Participants

Reaction Steps

A suspension of 3-methoxy-4-[3-(2-methylphenyl)ureido]phenylacetic acid methyl ester (19.43 g, Reference Example 32) in methanol (195 ml) was treated with sodium hydroxide solution (65 ml, 1N) and the mixture was heated at reflux for 1 hour giving a clear solution. The reaction mixture was cooled to room temperature and filtered. The filtrate was diluted to 390 ml with water, then heated to 50° C. and then acidified to pH 1 by the addition of hydrochloric acid (80 ml, 1N) over 1 hour. The resulting suspension was stirred for a further 30 minutes at 50° C., then allowed to cool to room temperature and then filtered. The solid was washed with twice with water (200 ml) then dried to give the title compound (15.72 g) as a white solid, m. p. 179-181° C. (with decomposition).

Provenance & Evidence