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