Title

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

Document Type

Article

Publication Date

4-26-2017

Department

Chemistry and Biochemistry

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

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