Hydrochloric Acid → 2-Chloro-6-methylamino-benzoic acid

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Reaction Steps

Sodium (3.35 g, 146 mmol) was slowly added to stirred MeOH (45 mL). Upon completion of gas evolution, 6-chloroanthranilic acid (5 g, 29 mmol) was added forming a suspension. This mixture was added to a separate flask containing a suspension of paraformaldehyde (1.22 g, 43.5 mmol) in MeOH (35 mL), and the resulting solution was stirred for 5 h at room temperature. Sodium borohydride (1.1 g, 29 mmol) was added and the mixture refluxed for 3 h. The cooled mixture was hydrolyzed with 1 M potassium hydroxide then neutralized to pH 3 using 2 M HCl. The precipitate was filtered to yield 2-chloro-6-methylamino benzoic acid (2.2 g, 41%).

Provenance & Evidence