Dimethyl Sulfoxide → HCID 67203841, compound

Participants

Reaction Steps

5-Amino-2-((2,2-dimethyl-1,3-dioxolan-4-yl)methyl)isoquinolin-1(2H)-one (4.2 g, 0.015 mol) was added to a solution of sodium nitrite (4 g, 0.06 mol) in dimethyl sulfoxide (80 mL, 1 mol) at 35° C. Aqueous hydrogen iodide (8 mL, 0.06 mol) in dimethyl sulfoxide (80 mL, 1 mol) was added, and the reaction mixture was stirred for 1 hour. The cooled reaction mixture was neutralized with sat. aq. NaHCO3 and extracted with methylene chloride (3×50 mL). The combined methylene chloride extracts were washed with brine, dried over magnesium sulfate. The solvent was removed in vacuo and the residue was purified via flash column chromatography (40 g of silica gel, 0-50% EtOAc/Hexane) to give a light yellow solid. MS m/z (M+H) 385.6

Provenance & Evidence