Development of Synthetic Route for 3-Amino-5-halo-2-iodobenzoates: Versatile Starting Materials in Pharmaceuticals Synthesis

Jinjae Park, Ju Ahn Seo, Cheol Hong Cheon

Research output: Contribution to journalArticlepeer-review

Abstract

A novel synthetic route to 3-amino-5-halo-2-iodobenzoates, which are used as versatile starting materials in the synthesis of pharmaceuticals, was developed using commercially available 2-aminobenzoates bearing a suitable halogen atom at the C5 position as the starting material. Synthesis was initiated with the introduction of a nitro group at the C3 position of the appropriate 2-aminobenzoates, forming 2-amino-3-nitrobenzoates with a C5-halogen atom. The subsequent conversion of the C2-amino group to an iodide yielded 5-halo-2-iodo-3-nitrobenzoates, which were further converted into the desired 3-amino-5-halo-2-iodobenzoates by reducing the C3-nitro group to an amino group. It is worth noting that this transformation can be conducted on a 50 mmol scale, and the desired benzoate compounds were obtained in good yield, demonstrating the practical applicability of this protocol.

Original languageEnglish
Article numbere202400027
JournalAsian Journal of Organic Chemistry
Volume13
Issue number5
DOIs
Publication statusPublished - 2024 May

Bibliographical note

Publisher Copyright:
© 2024 Wiley-VCH GmbH.

Keywords

  • 1,2,3,5-tetrasubstituted benzenoid
  • 3-amino-5-halo-2-iodobenzoates
  • Sandmeyer reaction
  • nitration
  • starting material synthesis

ASJC Scopus subject areas

  • Organic Chemistry

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