Hydrochloric Acid → Isoquinoline, 6-hydroxy-1,2,3,4-tetrahydro-, hydrochloride

HRID 1061041Notes

Reaction equation

HRID 1061041 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH2:9][NH:8][CH2:7][CH2:6]2.[Cl-:13].[Al+3].[Cl-].[Cl-].Cl.C(=O)(O)[O-].[Na+]>CSC.O.ClCCl>[ClH:13].[OH:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH2:9][NH:8][CH2:7][CH2:6]2

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 393566-Methoxy-1,2,3,4-tetrahydroisoquinolineHCID 516892Sodium BicarbonateHCID 6451240Aluminum(III) Chloride

Product 1

HCID 2752309Isoquinoline, 6-hydroxy-1,2,3,4-tetrahydro-, hydrochloride

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1068Dimethyl SulfideSolventHCID 6344DichloromethaneSolvent

Procedure

In dimethylsulfide (20 ml), 6-methoxy-1,2,3,4-tetrahydroisoquinoline (7.75 g) was dissolved, followed by the addition of aluminum chloride (19.0 g) under ice cooling. The resulting mixture was stirred at room temperature for 3 hours. Dichloromethane and dilute hydrochloric acid were added to the reaction mixture. A saturated aqueous solution of sodium bicarbonate was added to the water layer so separated to make it weakly alkaline, followed by the extraction with dichloromethane. After drying over anhydrous sodium sulfate, the solvent was then distilled off under reduced pressure. The residue was dissolved in saturated ethanol hydrochloride (100 ml) and the solvent was distilled off under reduced pressure. Ethyl acetate was added to the residue and the solid so precipitated was collected by filtration, whereby the title compound (7.91 g, 90%) was obtained.

Workup

  1. customso separated
  2. extractionfollowed by the extraction with dichloromethane
  3. dry with materialAfter drying over anhydrous sodium sulfate
  4. distillationthe solvent was then distilled off under reduced pressure
  5. dissolutionThe residue was dissolved in saturated ethanol hydrochloride (100 ml)
  6. distillationthe solvent was distilled off under reduced pressure
  7. additionEthyl acetate was added to the residue
  8. customthe solid so precipitated
  9. filtrationwas collected by filtration, whereby the title compound (7.91 g, 90%)
  10. customwas obtained

Sources & evidence

ORD record
ord-c8193f23d0e5407cab177538d332f72a
Source dataset
uspto-grants-2003_02
Patent number
US06525042B1

Reaction notes

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