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Autoxidation of 3-Hydroxyanthranilic Acid

Journal Article


Abstract


  • 3-Hydroxyanthranilic acid in aqueous solution can be autoxidized to yield two different products depending on the pH at which the oxidation is performed. At acidic pH the formation of cinnabarinic acid is favored while at alkaline pHs the major product is a newly characterized p-quinone dimer. Both of these oxidation products are formed at pH 7. A mechanism to account for these pH-dependent oxidations is proposed. © 1988, American Chemical Society. All rights reserved.

Publication Date


  • 1988

Citation


  • Manthey, M. K., Pyne, S. G., & Truscott, R. J. W. (1988). Autoxidation of 3-Hydroxyanthranilic Acid. Journal of Organic Chemistry, 53(7), 1486-1488. doi:10.1021/jo00242a026

Scopus Eid


  • 2-s2.0-0039353419

Web Of Science Accession Number


Start Page


  • 1486

End Page


  • 1488

Volume


  • 53

Issue


  • 7

Abstract


  • 3-Hydroxyanthranilic acid in aqueous solution can be autoxidized to yield two different products depending on the pH at which the oxidation is performed. At acidic pH the formation of cinnabarinic acid is favored while at alkaline pHs the major product is a newly characterized p-quinone dimer. Both of these oxidation products are formed at pH 7. A mechanism to account for these pH-dependent oxidations is proposed. © 1988, American Chemical Society. All rights reserved.

Publication Date


  • 1988

Citation


  • Manthey, M. K., Pyne, S. G., & Truscott, R. J. W. (1988). Autoxidation of 3-Hydroxyanthranilic Acid. Journal of Organic Chemistry, 53(7), 1486-1488. doi:10.1021/jo00242a026

Scopus Eid


  • 2-s2.0-0039353419

Web Of Science Accession Number


Start Page


  • 1486

End Page


  • 1488

Volume


  • 53

Issue


  • 7