Phosphorus pentachloride → 4,4-Dimethyl-1,2,3,4-tetrahydroisoquinolin-1-one

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Reaction Steps

The compound (1.3 g) obtained in step (d) just above was dissolved in diethyl ether (15 ml). Phosphorus pentachloride (1.1 g) was added to the solution. The mixture was stirred at room temperature for 30 min. The solvent was then removed by distillation under the reduced pressure. Glyme (20 ml) and sodium boron hydride (1.1 g) were added to the residue. The mixture was stirred at room temperature for one hr. Water was added to the reaction solution, followed by stirring. The mixture was then extracted with ethyl acetate. The organic layer was then dried over anhydrous magnesium sulfate. The solvent was then removed by distillation under the reduced pressure. The residue was purified by column chromatography on silica gel (chloroform:methanol=30:1) to give 4,4-dimethyl-3,4-dihydro-2H-isoquinolin-1-one (1.8 g).

Provenance & Evidence