Sodium Methoxide → 7-Fluoro-2-methoxy-8-methylquinoxaline

HRID 2233167Notes

Reaction equation

HRID 2233167 reaction equation
Cl[C:2]1[CH:11]=[N:10][C:9]2[C:4](=[C:5]([CH3:13])[C:6]([F:12])=[CH:7][CH:8]=2)[N:3]=1.[CH3:14][O-:15].[Na+]>CO>[F:12][C:6]1[C:5]([CH3:13])=[C:4]2[C:9]([N:10]=[CH:11][C:2]([O:15][CH3:14])=[N:3]2)=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 866283592-Chloro-7-fluoro-8-methylquinoxaline

Product 1

HCID 675481507-Fluoro-2-methoxy-8-methylquinoxalineYield 96%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

2-Chloro-7-fluoro-8-methylquinoxaline (4.1 g, 20.9 mmol) was suspended in dry methanol and a 25% solution of sodium methoxide in methanol (4.73 ml, 21.9 mmol) was added by syringe. The mixture was heated under reflux for 2 h, then evaporated. The residue was dissolved in dichloromethane and water and the phases were separated. The aqueous phase was extracted twice with dichloromethane, and combined organic fractions were dried and evaporated to give product (3.84 g, 96%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 2 h
  3. customevaporated
  4. dissolutionThe residue was dissolved in dichloromethane
  5. customwater and the phases were separated
  6. extractionThe aqueous phase was extracted twice with dichloromethane
  7. customwere dried
  8. customevaporated

Sources & evidence

ORD record
ord-a142b70347a1436ba085ad7f7903088e
Source dataset
uspto-grants-2010_05
Patent number
US07709483B2

Reaction notes

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