Acetic Anhydride → 2,2'-[[2-[(4-Bromo-3-methylphenyl)amino]-2-oxoethyl]imino]bisacetic acid

Participants

Reaction Conditions

Reaction Steps

A slurry of 9.56 g of nitrilotriacetic acid in 80 ml of dry pyridine (dried over molecular sieves) is heated to 55° C. Acetic anhydride (7.66 g) is added and the solution is heated to 100° C. After heating for 0.5 hour, the solution is cooled to 55° C. and 9.30 g of 4-bromo-3-methylaniline is added with a 5 ml pyridine rinse. The solution is heated at 100° C. for 1.0 hour. The reaction is cooled and rotary evaporated to a pasty solid which is dissolved in 120 ml of aqueous ammonium hydroxide (30 ml concentrated ammonium hydroxide/90 ml distilled water). The clear brown solution is extracted with two 100 ml portions of methylene chloride and neutralized to pH 3 with 35 ml of concentrated HCl. The white solid is filtered, washed with three 25 ml portions of cold distilled water, and dried under vacuum for 2.75 hours at 60° C. The crude product (12.9 g) is recrystallized from 360 ml of 50% ethanol to give 9.85 g of product, melting point 206.5°-209.0° C.

Provenance & Evidence