• 10.1021/jo0518809
  • The Journal of Organic Chemistry
  • Volume 71
  • January 2006
  • pp 142-149

Synthesis of N-(4-carboxyphenyl) anthranilic acid

Details


N-(4-carboxyphenyl) anthranilic acid (compound 31)

A mixture of 2-chlorobenzoic acid (1 mmol), 4-aminobenzoic acid (1 mmol), K2CO3 (2 mmol), Cu powder (0.009 mmol), and Cu2O (0.009 mmol) in 0.3 mL of 2-ethoxyethanol was refluxed at 130°C under inert atmosphere for 24 h. The cooled reaction mixture was poured into 3 mL of water. Charcoal was then added, and the solution was filtered through Celite. The crude product was obtained by precipitation upon acidification of the filtrate with diluted HCl. The residue was dissolved in 10 mL of 5% aqueous Na2CO3 solution and filtered through Celite, and the final product was isolated by precipitation upon careful pH adjustment. (0.169 g, yield=66%), 1H-NMR (300MHz, CDCl3) δ: 6.82 (dd, 1H), 7.08 (d, 1H), 7.14 (d, 1H), 7.26-7.30 (m, 3H), 7.40 (dd,1H), 8.06 (d, 1H), 9.32 (bs, 1H). 13C-NMR (300MHz, CDCl3) δ: 171.5, 168.3, 146.2, 145.1, 136.0, 131.1, 130.0, 124.5, 119.6, 117.5, 116.3, 115.1.



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