Acetic Acid → Methyl 1-oxo-1,2-dihydroisoquinoline-3-carboxylate

Participants

Reaction Steps

A solution of methyl isocyanoacetate (4.20 mL, 46.2 mmol) and methyl 2-formylbenzoate (6.90 g, 42.0 mmol) in 30 mL of N,N-dimethylformamide was added dropwise to a suspension of sodium hydride (1.21 g, 50.4 mmol) in 20 mL of N,N-dimethylformamide. After 5 hr, the mixture was treated with 10% aqueous acetic acid and water and extracted 2× with ethyl acetate. The combined organic extracts were washed 3× with water and brine, dried with sodium sulfate, filtered, and concentrated in vacuo. The residue was crystallized from 1:10 ethyl acetate:hexanes to provide methyl 1-oxo-1,2-dihydroisoquinoline-3-carboxylate.

Provenance & Evidence