Hydrochloric Acid → (6-Methoxy-4-isoquinolinyl)methanol hydrochloride

HRID 1350081Notes

Reaction equation

HRID 1350081 reaction equation
[ClH:1].[CH3:2][O:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[CH:10]=[N:9][CH:8]=[C:7]2[C:14](OC)=[O:15].[H-].[Al+3].[Li+].[H-].[H-].[H-].Cl>CCOCC.[OH-].[Na+]>[ClH:1].[CH3:2][O:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[CH:10]=[N:9][CH:8]=[C:7]2[CH2:14][OH:15]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 21094288HCID 21094288, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 21094271(6-Methoxy-4-isoquinolinyl)methanol hydrochloride

Reagents, catalysts & solvents 2

HCID 14798Sodium HydroxideCatalystHCID 3283Diethyl EtherSolvent2×

Procedure

The compound obtained in Step A (0.395 g; 0.0015 mol), in the form of a base, is dissolved in 200 ml of ether. Lithium aluminium hydride (0.14 g; 0.004 mol) is then progressively added while cooling the flask in ice. The reaction mixture is stirred at ambient temperature for one week. A minimum of 30% sodium hydroxide solution (a few drops) is added to the reaction mixture to form the precipitates of lithium and aluminium hydroxides. The precipitates are then filtered off and washed with ethyl acetate. The organic phase is dried over magnesium sulphate, filtered and evaporated under reduced pressure. The oil obtained is taken up in ether saturated with HCl(g). The precipitate formed is suction-filtered off and recrystallised from acetonitrile to yield the title product in the form of a white solid.

Workup

  1. temperaturewhile cooling the flask in ice
  2. customto form the
  3. customprecipitates of lithium and aluminium hydroxides
  4. filtrationThe precipitates are then filtered off
  5. washwashed with ethyl acetate
  6. dry with materialThe organic phase is dried over magnesium sulphate
  7. filtrationfiltered
  8. customevaporated under reduced pressure
  9. customThe oil obtained
  10. customThe precipitate formed
  11. filtrationis suction-filtered off
  12. customrecrystallised from acetonitrile

Sources & evidence

ORD record
ord-d5a147d4156d4cb3b6bb9d090c51373e
Source dataset
uspto-grants-2007_05
Patent number
US07214689B2

Reaction notes

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