Dimethyl Sulfoxide → (R)-2-(5-Iodo-1-oxoisoquinolin-2(1H)-yl)propyl acetate

Participants

Reaction Steps

Acetic acid (R)-2-(5-amino-1-oxo-1H-isoquinolin-2-yl)-propyl ester (790 mg, 0.0030 mol) was added to a solution of sodium nitrite (800 mg, 0.01 mol) in dimethyl sulfoxide (10 mL, 0.1 mol) at room temperature. Aqueous hydrogen iodide (4 mL, 0.03 mol) in dimethyl sulfoxide (10 mL, 0.1 mol) was added. The reaction mixture was stirred at room temperature for 1 hour. The cooled reaction mixture was neutralized with saturated aq. Na2CO3 and extracted with methylene chloride (3×100 mL). The combined methylene chloride extracts were washed with brine and dried over magnesium sulfate. The solvent was removed in vacuo and the residue was chromatographed on 40 of silica gel column (0-50% EtOAc/Hexane) to give the desired product as a brown oil. MS m/z (M+H) 371.9

Provenance & Evidence