Synthesis of [¹³C₆]3,4-Diaminobenzoic Acid as a Precursor for Stable Isotope Labeled Benzimidazoles

Authors

Matthew G. Donahue, University of Southern MississippiFollow
Nicholas G. Jentsch, University of Southern Mississippi
Casey R. Simons, University of Southern Mississippi

Document Type

Article

Publication Date

4-26-2017

Department

Chemistry and Biochemistry

School

Mathematics and Natural Sciences

Abstract

The synthesis of [¹³C₆]3,4-diaminobenzoic acid from commercially available [¹³C₆]aniline is described in six steps. Salient features of this route include the preparation of a differentially protected 3,4-diaminobenzonitrile, hydrogen gas free aromatic nitro group reduction with ammonium formate and facile benzimidazole ring closure of the ortho-arylenediamine with triethylorthoformate. This stable-labeled 3,4-diaminobenzoic acid is an ideal [M+6]isotopomer to synthesize complex benzimidazole fragments for mass spectrometry internal assays.

Publication Title

Tetrahedron Letters

Volume

58

Issue

17

First Page

1692

Last Page

1694

Recommended Citation

Donahue, M. G., Jentsch, N. G., Simons, C. R. (2017). Synthesis of [¹³C₆]3,4-Diaminobenzoic Acid as a Precursor for Stable Isotope Labeled Benzimidazoles. Tetrahedron Letters, 58(17), 1692-1694.
Available at: https://aquila.usm.edu/fac_pubs/15298