Synthesis of [13C6]3,4-diaminobenzoic acid as a precursor for stable isotope labeled benzimidazoles
2017
Donahue, Matthew G. | Jentsch, Nicholas G. | Simons, Casey R.
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.
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