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

HRID 352857Notes

Reaction equation

HRID 352857 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-].[Al+3].[Cl-].[Cl-].[Cl:17]CCl.Cl>CSC>[ClH:17].[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

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 393566-Methoxy-1,2,3,4-tetrahydroisoquinolineHCID 6451240Aluminum(III) Chloride

Product 1

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

Reagents, catalysts & solvents 1

HCID 1068Dimethyl SulfideSolvent

Procedure

In dimethyl sulfide (20 ml), 6-methoxy-1,2,3,4-tetrahydroisoquinoline (7.75 g) was dissolved. Under ice cooling, aluminum chloride (19.0 g) was added to the resulting solution, followed by stirring at room temperature for 3 hours. Dichloromethane and dilute hydrochloric acid were added to separate the water layer. The water layer was made basic by the addition of a saturated aqueous solution of sodium bicarbonate, followed by extraction with dichloromethane. The extract was dried over anhydrous sodium sulfate and distilled under reduced pressure to remove the solvent. The residue was dissolved in saturated solution of hydrochloride in ethanol (100 ml). To the residue obtained by distilling off the solvent under reduced pressure, ethyl acetate was added. The solid thus precipitated was collected by filtration, whereby the title compound (7.91 g, 90%) was obtained.

Workup

  1. customto separate the water layer
  2. additionThe water layer was made basic by the addition of a saturated aqueous solution of sodium bicarbonate
  3. extractionfollowed by extraction with dichloromethane
  4. dry with materialThe extract was dried over anhydrous sodium sulfate
  5. distillationdistilled under reduced pressure
  6. customto remove the solvent
  7. dissolutionThe residue was dissolved in saturated solution of hydrochloride in ethanol (100 ml)
  8. customTo the residue obtained
  9. distillationby distilling off the solvent under reduced pressure, ethyl acetate
  10. additionwas added
  11. customThe solid thus precipitated
  12. filtrationwas collected by filtration, whereby the title compound (7.91 g, 90%)
  13. customwas obtained

Sources & evidence

ORD record
ord-aa455968dc354d0386c7863d2402d1a2
Source dataset
uspto-grants-2004_06
Patent number
US06747023B1

Reaction notes

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