3,4-Dihydro-6,7-dimethoxy-1-methylisoquinoline → HCID 54178010, compound

Participants

Reaction Steps

10.3 g (50.0 mmol) of 1-methyl-6,7-dimethoxy-3,4-dihydroisoquinoline, 8.3 g (55.0 mmol) of methyl 4-chloroacetoacetate and 12.6 g (150 mmol) of sodium hydrogen carbonate in 100 ml of ethanol are heated at reflux for 5 hours. After evaporation to dryness, the residue is taken up in 250 ml of dichloromethane and washed twice with 100 ml of water each time. After drying the organic phase over magnesium sulphate and then concentrating, the residue (15.5 g) is chromatographed on 500 g of silica (eluant: dichloromethane) to yield 8.5 g of the expected product (theory: 15.1 g).

Provenance & Evidence