Water → HCID 178522814, compound

Participants

Reaction Steps

To a solution of 2-benzamido-N-benzyl-6-methoxyisonicotinamide (0.18 g, 0.50 mmol) and sodium iodide (0.45 g, 3.00 mmol) in acetonitrile (10 mL) was added chlorotrimethylsilane (0.39 mL, 3.00 mmol) and water (0.1 mL) at 0° C. The resulting solution was stirred at ambient temperature for 20 hours, quenched with methanol (10 mL), stirred for 10 minutes and concentrated in vacuo. The residue was washed with saturated sodium bicarbonate solution (5 mL) and water (5 mL). The organic solution was dried over anhydrous sodium sulphate, filtered and concentrated in vacuo to a minimum volume and triturated with ethyl acetate. The solid was filtered and dried in vacuo to give 2-benzamido-N-benzyl-6-hydroxyisonicotinamide as a colorless solid (0.04 g, 20%): mp 257° C. (dec); 1H NMR (300 MHz, DMSO-d6) δ 11.07 (br s, 1H), 9.20 (br s, 1H), 8.46-6.59 (m, 12H), 4.37 (br s, 2H); MS (ES+) m/z 348.5 (M+1).

Provenance & Evidence