Formic Acid → HCID 69069868, compound

Participants

Reaction Steps

A suspension of 4-{[3-(acetylamino)phenyl]amino}-3-nitrobenzoic acid (1.27 g, 4.04 mmol) and iron powder (1.77 g, 31.6 mmol) in HCO2H (30 mL) and HC(OMe)3 (20 mL) was stirred at rt under N2 atmosphere. After 18 h, the reaction mixture was filtered through Celite and the Celite pad was washed with EtOH. The solvent was removed in vacuo. The resultant crude material was purified by silica gel chromatography (10% MeOH in CH2Cl2) to afford 1-[3-(acetylamino)phenyl]-1H-benzimidazole-5-carboxylic acid as a light yellow solid. 1H NMR (400 MHz, DMSO-d6): δ 2.07 (s, 3H), 7.36 (d, J=8.4 Hz, 1H), 7.56 (t, J=8.0 Hz, 1H), 7.63 (d, J=8.4 Hz, 1H), 7.69 (d, J=8.8 Hz, 1H), 7.96 (d, J=8.8 Hz, 1H), 8.02 (s, 1H), 8.34 (s, 1H), 8.71 (s, 1H), 10.3 (s, 1H). MS (ES+): m/z 296 [MH+].

Provenance & Evidence