Quinone → HCID 178509507, compound

Participants

Reaction Steps

A mixture comprising 2-pyridinecarboxaldehyde (212 mg, 1.98 mmol, 1 eq), 3,4-diaminobenzonitrile (263 mg, 1.98 mmol, 1 eq) and ethanol (20 mL) was stirred at ambient temperature under nitrogen for 5 to 10 minutes and then 1,4-benzoquinone (233 mg, 2.16 mmol, 1.2 eq) was added. The mixture was heated at reflux for 3 hours and then concentrated. The residue was partitioned between ethyl acetate and saturated sodium bicarbonate. The organic layer was separated, dried (MgSO4), filtered and concentrating to dryness to provide 2-pyridin-2-yl-1H-benzimidazole-5-carbonitrile (348 mg, 1.58 mmol) as an off white solid; ESI LC/MS: 261.9=(MH+ +CH3CN); 1H-NMR (300 Mhz, DMSO-d6): 7.65-7.755 (m, 2H), 7.769 (d, 1H), 8.060 (t, 1H), 8.163 (s, 1H), 8.395 (d, 1H), 8.772 (d, 1H).

Provenance & Evidence