2,3-Diaminobenzoic acid → 2-(6-chloropyridin-3-yl)-1H-benzo[d]imidazole-4-carboxylic acid

Participants

Reaction Conditions

Reaction Steps

2,3-Diaminobenzoic acid (1; 200 mg, 1.31 mmol), 6-chloronicotinaldehyde (5; 186 mg, 1.31 mmol), and Na2S2O5 (324 mg, 1.7 mmol) were taken up in DMF (10 mL) and stirred at 100° C. for 18 h. The reaction mixture was cooled to room temperature and diluted with H2O. The resulting mixture was stirred for 1 h at room temperature and filtered. The collected solids were washed with water, MeOH, and dried to afford 2-(6-chloropyridin-3-yl)-1H-benzo[d]imidazole-4-carboxylic acid 6 as a pale solid (340 mg, yield: 95%).

Provenance & Evidence