Synthesis of N-aryl and N-alkyl anthranilic acids via S(N)Ar reaction of unprotected 2-fluoro- and 2-methoxybenzoic acids by lithioamides

Org Lett. 2010 May 21;12(10):2406-9. doi: 10.1021/ol1007586.

Abstract

Substitution of the fluoro or methoxy group in unprotected 2-fluoro- and 2-methoxybenzoic acids to afford N-aryl and N-alkyl anthranilic acids occurs upon reaction with lithioamides under mild conditions in the absence of a metal catalyst.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amides / chemistry*
  • Benzoates / chemistry*
  • Lithium / chemistry*
  • Molecular Structure
  • Organometallic Compounds / chemistry*
  • Stereoisomerism
  • ortho-Aminobenzoates / chemical synthesis*
  • ortho-Aminobenzoates / chemistry

Substances

  • Amides
  • Benzoates
  • Organometallic Compounds
  • ortho-Aminobenzoates
  • Lithium