Hydrochloric Acid → 4-Amino-5-chloro-2-[2-(diethylamino)-2-oxoethoxy]benzoic acid

Participants

Reaction Conditions

Reaction Steps

A solution of 4-amino-5-chloro-2-[2-(diethylamino)-2-oxoethoxy]benzoic acid, methyl ester (7.87 g, 25 mmol) in water (70 g) containing methanol (40 g) was treated with 50% sodium hydroxide (10 g) and heated to 60° C. for 30 minutes. The mixture was neutralized with 3N HCl until a precipitate formed (pH 3), and the solid was collected, washed with water, air dried, and recrystallized from 2-propanol to afford (2 crops) 5.12 g (68%) of fine colorless needles; mp 186.5°-188.0° C.

Provenance & Evidence