Anthranilic Acid → 2-[(Sulfomethyl)amino]benzoic acid

Participants

Reaction Conditions

Reaction Steps

Formaldehyde solution (37%, 31.6 g, 0.4 mol) and sodium bisulfite (38 g, 0.37 mol) were dissolved in water (200 ml) and the stirred mixture warmed to 60° C. Anthranilic acid (50 g, 0.37 mol) was dissolved in water (200 ml) at pH 7, and this solution was added to the bisulfite adduct solution, maintaining the temperature at 60-70° C. for 2 hours. The reaction mixture was allowed to cool slowly before hydrochloric acid was added to precipitate the product as a white solid. The product was collected by filtration and washed with saturated sodium chloride solution and then acetone. The dried product (34 g) contained 22.5% salt.

Provenance & Evidence