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

HRID 845833Notes

Reaction equation

HRID 845833 reaction equation
CC(C)([O-])C.[K+].[OH:7][CH:8]1[C:17]2[C:12](=[C:13]([O:21][CH3:22])[C:14]3[O:20][CH2:19][O:18][C:15]=3[CH:16]=2)[CH2:11][N:10]([CH3:23])[CH2:9]1.C1(=O)C2C(C3C(C=2)=CC=CC=3)=CC=C1>C1C=CC=CC=1>[CH3:22][O:21][C:13]1[C:14]2[O:20][CH2:19][O:18][C:15]=2[CH:16]=[C:17]2[C:12]=1[CH2:11][N:10]([CH3:23])[CH2:9][C:8]2=[O:7]

Participants

5

Reactant 3

HCID 13912214HCID 13912214, compoundHCID 22281833FluoreneoneHCID 23665647Potassium tert-butoxide

Product 1

HCID 139122192,3-dihydro-8-methoxy-2-methyl-6,7-methylenedioxy-4(1H)-isoquinoloneYield 8.2%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

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.

Workup

  1. temperaturerefluxed
  2. temperatureunder heating for 10 minutes
  3. customthe reaction
  4. extractionThe solution was extracted with ethyl ether
  5. extractionthe organic layer was extracted with a 5% hydrochloric acid solution
  6. extractionextracted with ether
  7. customdried
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe resulted residue was purified by silica gel column chromatography (eluent: 4% methanol/chloroform)

Sources & evidence

ORD record
ord-3b2d56cbf7ac49ccbe31370cfd2b6750
Source dataset
uspto-grants-1988_07
Patent number
US04760145

Reaction notes

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