Dimethyl Sulfoxide → HCID 58270431, compound

Participants

Reaction Steps

5-Amino-2-cyclopropylisoquinolin-1(2H)-one (2.0 g, 0.0095 mol) was added to a solution of sodium nitrite (3 g, 0.04 mol) in dimethyl sulfoxide (100 mL, 2 mol) at room temperature. Aqueous hydrogen iodide (10 mL, 0.08 mol) in dimethyl sulfoxide (100 mL, 2 mol) was added. The reaction mixture was stirred at room temperature for 1 hour. The reaction mixture was neutralized with saturated aq. Na2CO3 and extracted with methylene chloride (3×200 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 120 g of silica gel column (0-25% EtOAc/Hexane) to give the desired product as a yellow solid. MS m/z (M+H) 312.2.

Provenance & Evidence