Hydrochloric Acid → 4-((((Pyridin-3-ylmethoxy)carbonyl)amino)methyl)benzoic acid

Participants

Reaction Steps

A N,N-dimethylformamide (150 ml) solution including 65.4 g (0.6 mole) of 3-pyridinemethanol was added dropwise to a N,N-dimethylformamide (300 ml) suspension including 97.2 g (0.6 mole) of N,N′-carbonyldiimidazole at an internal temperature of 10° C. or less. The mixture was then added dropwise to a separately prepared 1 N aqueous sodium hydroxide solution (455 ml) including 75.5 g (0.5 mole) of 4-aminomethylbenzoic acid, followed by stirring at room temperature for 6 hours. To the resultant reaction mixture, a saturated sodium chloride solution was added, and concentrated hydrochloric acid was further added, thereby neutralizing the solution. After aging at 5° C. for 2 hours, the deposited white solid was collected by filtration, washed with water and methanol, and then dried to obtain 140 g (yield: 98%) of 4-[N-(pyridin-3-ylmethoxycarbonyl)amino-methyl]benzoic acid.

Provenance & Evidence