Sodium Bicarbonate → 2,3-Dimethyl-6-methoxy-4-phenylisoquinolinium hydroxide

HRID 639878Notes

Reaction equation

HRID 639878 reaction equation
[CH3:1][N:2]1[C:11]([CH3:12])=[C:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:19][CH3:20])[CH:8]=2)[C:3]1=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].C(=O)(O)[O-].[Na+].CCCCCC.C(OCC)(=O)C>O1CCCC1>[OH-:19].[CH3:1][N+:2]1[C:11]([CH3:12])=[C:10]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:19][CH3:20])[CH:8]=2)[CH:3]=1

Participants

6

Reactant 4

HCID 516892Sodium BicarbonateHCID 21226206Ethyl acetate hexaneHCID 21226445Aluminium lithium hydrideHCID 225559912,3-dimethyl-6-methoxy4-phenyl-2H-isoquinolin-1-one

Product 1

HCID 113804992,3-Dimethyl-6-methoxy-4-phenylisoquinolinium hydroxide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 2,3-dimethyl-6-methoxy4-phenyl-2H-isoquinolin-1-one (prepared using the synthetic procedure previously described in WO 2002024655, 250 mg, 0.896mmol) in tetrahydrofuran (10 mL) at room temperature under argon was added by dropwise addition a solution of lithium aluminum hydride (1.0 M, 0.896 mL, 0.896 mmol). The contents of the reaction flask were heated to reflux for 0.5 h, cooled to room temperature and carefully poured onto ice. Saturated sodium bicarbonate was added and the resulting mixture extracted with ethyl acetate (3×). The combined organic extracts were washed with brine and then dried with sodium sulfate (anh.). Filtration followed by removal of the solvent in vacuo gave a brown oil which was subjected to flash column chromatography (hexane:ethyl acetate 90:10). Evaporation of fractions containing product gave a tan oil which was triturated with hot toluene to afford the title compound as a tan solid.

Workup

  1. customat room temperature
  2. temperatureThe contents of the reaction flask were heated
  3. temperatureto reflux for 0.5 h
  4. additioncarefully poured onto ice
  5. extractionthe resulting mixture extracted with ethyl acetate (3×)
  6. washThe combined organic extracts were washed with brine
  7. dry with materialdried with sodium sulfate (anh.)
  8. filtrationFiltration
  9. customfollowed by removal of the solvent in vacuo
  10. customgave a brown oil which
  11. customEvaporation of fractions
  12. additioncontaining product
  13. customgave a tan oil which
  14. customwas triturated with hot toluene

Sources & evidence

ORD record
ord-ae587e8c91624c7f8a21ed5e42fd49e5
Source dataset
uspto-grants-2010_04
Patent number
US07691879B2

Reaction notes

Loading…