Sodium Methoxide → HCID 24766191, compound

HRID 1470457Notes

Reaction equation

HRID 1470457 reaction equation
[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[CH3:12])[C:5](Cl)=[N:4][CH:3]=1.[CH3:14][O-:15].[Na+]>CO>[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[CH3:12])[C:5]([O:15][CH3:14])=[N:4][CH:3]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 247661904-Bromo-1-chloro-5-methylisoquinoline

Product 1

HCID 24766191HCID 24766191, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 4-bromo-1-chloro-5-methylisoquinoline (Intermediate-5) (5.0 g, 19.5 mmol) in dry MeOH (100 mL) was added NaOMe (1.3 g, 23.4 mmol) and the reaction mixture was refluxed overnight. Solvent was removed and the resultant crude product was extracted with EtOAc (2×200 mL), washed with water (2×100 mL), dried over Na2SO4, filtered and concentrated under reduced pressure to furnished the title compound (4.5 g, 93%).

Workup

  1. temperaturethe reaction mixture was refluxed overnight
  2. customSolvent was removed
  3. extractionthe resultant crude product was extracted with EtOAc (2×200 mL)
  4. washwashed with water (2×100 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6b82e8f8e4824b67a91895990ffbd6a8
Source dataset
uspto-grants-2015_04
Patent number
US09006442B2

Reaction notes

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