Hydrochloric Acid → HCID 67193464, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of sodium hydride (60% in mineral oil, 227 mg, 5.7 mmol) in dry pyridine (4 ml) was added dropwise a solution of methyl isoquinoline-3-carboxylate (390 mg, 2.08 mmol) and 2′-hydroxy-acetophenone (257 mg, 1.89 mmol) in dry pyridine (4 ml). The mixture was heated at 90° C. for 15 min., cooled to room temperature and poured into an ice cooled 1N hydrochloric acid aqueous solution. The product was extracted in dichloromethane. The organic layers were washed with a 1N hydrochloric acid solution, brine, dried over sodium sulfate and concentrated to dryness. The residue was dissolved in acetic acid (10 ml) and treated with sulfuric acid (40 μl). The solution was heated to 100° C. for 30 min. and cooled to room temperature. The solvents were removed under vacuum distillation. The solid was triturated in water, filtered, washed with a saturated solution of sodium hydrogenocarbonate and water. The solid was dried under vacuum to yield 2-Isoquinolin-3-yl-chromen-4-one (459 mg, 89%) as beige solid.

Provenance & Evidence