HCID 13912214, compound → 2,3-dihydro-8-methoxy-2-methyl-6,7-methylenedioxy-4(1H)-isoquinolone

Participants

Reaction Steps

673 mg (6 mmol) of potassium-t-butoxide was added to a solution (20 ml) of 593 mg (2.5 mmol) of 4-hydroxy-8-methoxy-2-methyl-6,7-methylenedioxy-1,2,3,4-tetrahydroisoquinoline (6) and 2.25 g (12.5 mmol) of fluorenone in anhydrous benzene under a nitrogen atmosphere and refluxed under heating for 10 minutes. Then 15 ml of ice-cold water was added to the solution to stop the reaction. The solution was extracted with ethyl ether and then the organic layer was extracted with a 5% hydrochloric acid solution. The aqueous layer was made basic, then extracted with ether, dried, filtered and concentrated. The resulted residue was purified by silica gel column chromatography (eluent: 4% methanol/chloroform) to obtain 48.1 mg of 2,3-dihydro-8-methoxy-2-methyl-6,7-methylenedioxy-4(1H)-isoquinolone (12) (yield: 8%). Melting point: 116°-119° C.

Provenance & Evidence