Dimethyl Sulfoxide → HCID 67203524, compound

Participants

Reaction Steps

5-Amino-2-(2-hydroxyethyl)isoquinolin-1(2H)-one (1.62 g, 0.00793 mol) was added to a solution of sodium nitrite (2 g, 0.03 mol) in dimethyl sulfoxide (40 mL, 0.5 mol) at 35° C. Aqueous hydrogen iodide (4 mL, 0.03 mol) in dimethyl sulfoxide (40 mL, 0.5 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 sodium sulfate and reduced in vacuo. The mixture was purified by column chromatography using an ethyl acetate:hexanes (0-100) gradient. The combined pure fractions were reduced in vacuo to yield the title compound as an off white solid.

Provenance & Evidence