Water → HCID 15239439, compound

HRID 1609494Notes

Reaction equation

HRID 1609494 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:18][C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11](=[O:19])[N:10]2[CH3:20])=[CH:5][CH:4]=1.[Cl-].[Al+3].[Cl-].[Cl-].O>C1C=CC=CC=1>[OH:2][C:3]1[CH:4]=[CH:5][C:6]([CH:9]2[CH2:18][C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11](=[O:19])[N:10]2[CH3:20])=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6451240Aluminum(III) ChlorideHCID 134476023-(4-Methoxyphenyl)-2-methyl-3,4-dihydroisoquinolin-1(2H)-one

Product 1

HCID 15239439HCID 15239439, compoundYield 56.4%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To 500 ml of a solution containing 10 g of 3-(4-methoxyphenyl)-2-methyl-1-oxo-1,2,3,4-tetrahydroisoquinoline in benzene, 20 g of aluminum chloride was added and the mixture was heated to reflux for 7 hours. After allowing the resulting mixture to cool, water was added thereto and the generated insoluble materials were removed by filtration through Celite. The filtrate was extracted with ethyl acetate and the combined organic layers were washed with brine, followed by drying over anhydrous magnesium sulfate. After evaporating the solvent, the residue was purified by silica gel column chromatography [hexane/ethyl acetate (2/1) to obtain 5.34 g of 3-(4-hydroxyphenyl)-2-methyl-1-oxo-1,2,3,4-tetrahydroisoquinoline.

Workup

  1. additionwas added
  2. temperaturethe mixture was heated
  3. temperatureto reflux for 7 hours
  4. temperatureto cool
  5. customthe generated insoluble materials were removed by filtration through Celite
  6. extractionThe filtrate was extracted with ethyl acetate
  7. washthe combined organic layers were washed with brine
  8. dry with materialby drying over anhydrous magnesium sulfate
  9. customAfter evaporating the solvent
  10. customthe residue was purified by silica gel column chromatography [hexane/ethyl acetate (2/1)

Sources & evidence

ORD record
ord-60017ae55f474b1bbf50e1ab4d989e70
Source dataset
uspto-grants-1995_03
Patent number
US05401752

Reaction notes

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