Tetrahydrofuran → HCID 19976049, compound

Participants

Reaction Steps

To a solution consisting of 7-nitro-1,2,3,4-tetrahydroisoquinolin-1-one (2.0 g, 10.4 mmol) in tetrahydrofuran (300 mL) was added sodium hydride (500 mg, 60% suspension in oil, 12.5 mmol). To the resulting mixture was added methyl bromoacetate (1.1 mL, 11 mmol). After 3 hours, ethyl acetate (20 mL) was added followed by water (25 mL). The solution was concentrated and the resulting oil was partitioned between ethyl acetate and water (1:1,200 mL). The layers were separated and the organic layer was washed successively with water (1×100 mL) and brine (1 ×100 mL). The organic layer was dried with anhydrous magnesium sulfate, filtered and concentrated. The residue was treated with ethyl acetate and a solid formed. The solution was filtered to give the title compound (1.6 g, 55% yield).

Provenance & Evidence