Anthranilic acid
Anthranilic acid (or o-amino-benzoic acid) is an aromatic acid with the formula C6H4(NH2)(CO2H). The molecule consists of a substituted benzene ring, hence is classed as aromatic, with two adjacent, or "ortho-" functional groups, a carboxylic acid and an amine. The compound is consequently amphoteric. In appearance, anthranilic acid is a white solid when pure, although commercial samples may appear yellow. It is sometimes referred to as vitamin L1 and has a sweetish taste. The anion [C6H4(NH2)(CO2)]−, obtained by the deprotonation of anthranilic acid, is called anthranilate.
Structure
Although not usually referred to as such, it is an amino acid. Solid anthranilic acid consists of both the amino-carboxylic acid and the zwitterionic ammonium carboxylate forms.
Production
Many routes to anthranilic acid have been described. Industrially it is produced from phthalic anhydride, beginning with amination:
The resulting sodium salt of phthalamic acid is decarbonylated via a Hofmann rearrangement of the amide group, induced by hypochlorite: