Water → HCID 15239363, compound

HRID 1609490Notes

Reaction equation

HRID 1609490 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)[CH2:11][N:10]2[CH3:19])=[CH:5][CH:4]=1.[Cl-].[Al+3].[Cl-].[Cl-].O>C1C=CC=CC=1>[OH: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)[CH2:11][N:10]2[CH3:19])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6451240Aluminum(III) ChlorideHCID 15239362HCID 15239362, compound

Product 1

HCID 15239363HCID 15239363, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To 30 ml of 3-(4-methoxyphenyl)-2-methyl-1,2,3,4-tetrahydroisoquinoline (Compound No. 19) in benzene, 0.85 g of aluminum chloride was added and the resulting mixture was heated to reflux for 5 hours. After completion of the reaction, the reaction mixture was allowed to cool and water was added thereto. The generated precipitates were removed by filtration through Celite. The filtrate was made alkaline with saturated aqueous sodium hydrogen carbonate solution, and the resultant was extracted with ethyl acetate. After drying the combined organic layers over anhydrous magnesium sulfate, the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography [hexane/ethyl acetate (1/1)] to obtain 0.28 g of 3-(4-hydroxyphenyl)-2-methyl-1,2,3,4-tetrahydroisoquinoline.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureto reflux for 5 hours
  3. customAfter completion of the reaction
  4. temperatureto cool
  5. customThe generated precipitates
  6. customwere removed by filtration through Celite
  7. extractionthe resultant was extracted with ethyl acetate
  8. dry with materialAfter drying the combined organic layers over anhydrous magnesium sulfate
  9. customthe solvent was evaporated under reduced pressure
  10. customThe residue was purified by silica gel column chromatography [hexane/ethyl acetate (1/1)]

Sources & evidence

ORD record
ord-1ba54ce1fdb34d96a8ad1c937452b0ff
Source dataset
uspto-grants-1995_03
Patent number
US05401752

Reaction notes

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