Dimethyl Sulfoxide → HCID 67202863, compound

Participants

Reaction Conditions

Reaction Steps

5-Amino-2-(4-fluorobenzyl)isoquinolin-1(2H)-one (0.6 g, 0.002 mol) was added to a solution of sodium nitrite (0.5 g, 0.008 mol) in dimethyl sulfoxide (10 mL, 0.1 mol) at 35° C. Aqueous hydrogen iodide (2 mL, 0.02 mol) in dimethyl sulfoxide (10 mL, 0.1 mol) was added. The reaction mixture was stirred at 35° C. for 1 hour. The cooled reaction mixture was neutralized with saturated aq. Na2CO3 and extracted with methylene chloride (3×20 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 12 g of silica gel column (0-50% EtOAc/Hexane) gave the desired product as a brown solid. MS m/z (M+H) 379.7.

Provenance & Evidence