Acetic Acid → HCID 69023094, compound

Participants

Reaction Steps

To 1-benzyl-2-methylsulfanyl-1H-imidazo[4,5-c][1,5]naphthyridine (1 g, 3.2 mmol) was added acetic acid (15 mL), and the white suspension was stirred for a few minutes. To this suspension was added potassium permanganate solution (0.87 g, 5.5 mmol, in water (15 mL)) in a dropwise manner, and the reaction was stirred at room temperature for 2 hours. To the reaction mixture was added sodium bisulfite (0.83 g) and the white suspension was stirred for several minutes. Water was added to this suspension and the reaction mixture was transferred to a separatory funnel. The product was extracted from the aqueous layer with several batches of dichloromethane. The dichloromethane layers were combined, dried (MgSO4), filtered, and evaporated, and the resultant solid washed with ether to afford 1-benzyl-2-methanesulfonyl-1H-imidazo[4,5-c][1,5]naphthyridine as a white solid (0.9 g), mp 187-191° C.; MS (ESI) m/z 339 (M+H); Anal. Calcd for C17H14N4O2S: C, 60.34; H, 4.17; N, 16.56. Found C, 60.45; H, 3.97; N, 16.52.

Provenance & Evidence