Water → 8-Bromo-3-methoxyisoquinoline

HRID 1181412Notes

Reaction equation

HRID 1181412 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[CH:10]=[N:9][C:8]([OH:12])=[CH:7]2.IC.O.[C:16](OCC)(=O)C>CN(C=O)C.C(=O)([O-])[O-].[Ag+2]>[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[CH:10]=[N:9][C:8]([O:12][CH3:16])=[CH:7]2

Participants

7

Reactant 4

HCID 962WaterHCID 6328Methyl iodide2×HCID 8857Ethyl AcetateHCID 178515316HCID 178515316, compound

Product 1

HCID 522706578-Bromo-3-methoxyisoquinolineYield 22%

Reagents, catalysts & solvents 2

HCID 178418647HCID 178418647, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a suspension of 8-bromoisoquinolin-3-ol (Description 53; 7.3 g, 0.03 mol) and silver carbonate (13.6 g, 0.05 mol) in dry DMF (380 ml) under nitrogen was added iodomethane (2.25 ml, 0.04 mol). The mixture was stirred at 50° C. for 24 hours. Further iodomethane (1 ml, 0.015 mol) was added and the mixture heated for 64 hours at 50° C. The mixture was cooled, water (300 ml) and ethyl acetate (300 ml) were added and shaken well. The mixture was filtered through Celite™, the layers separated and the aqueous layer was extracted with ethyl acetate (3×50 ml). The organic layers were combined, evaporated to ˜150 ml, washed twice with water and then brine. The organic extract was then evaporated to give the title compound (1.7 g, 22%).

Workup

  1. temperaturethe mixture heated for 64 hours at 50° C
  2. temperatureThe mixture was cooled
  3. stirringshaken well
  4. filtrationThe mixture was filtered through Celite™
  5. customthe layers separated
  6. extractionthe aqueous layer was extracted with ethyl acetate (3×50 ml)
  7. customevaporated to ˜150 ml
  8. washwashed twice with water
  9. extractionThe organic extract
  10. customwas then evaporated

Sources & evidence

ORD record
ord-b5dcd5eb455c4fed9a123c3ac510da1c
Source dataset
uspto-grants-2007_10
Patent number
US07285563B2

Reaction notes

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