2-chloro-6-nitroquinoxaline → 2-Methoxy-6-nitroquinoxaline

HRID 1593386Notes

Reaction equation

HRID 1593386 reaction equation
Cl[C:2]1[CH:11]=[N:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([N+:12]([O-:14])=[O:13])[CH:8]=2)[N:3]=1.[CH3:15][O-:16].[Na+]>C1COCC1>[CH3:15][O:16][C:2]1[CH:11]=[N:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([N+:12]([O-:14])=[O:13])[CH:8]=2)[N:3]=1

Participants

4

Reactant 2

HCID 2357142-chloro-6-nitroquinoxalineHCID 10942334Sodium Methoxide

Product 1

HCID 150258562-Methoxy-6-nitroquinoxalineYield 68.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Into 10 ml of THF was dissolved 1.16 g of 2-chloro-6-nitroquinoxaline, and then 1.0 g of sodium methoxide was added thereto, followed by heating under refluxing for 30 minutes. Then, the solvent was removed by evaporation. Water was added to the residue, followed by extraction with ethyl acetate. The organic layer was washed with saturated saline. After the solvent was removed by evaporation, the residue was crystallized from diethyl ether-hexane to obtain 776 mg of the title compound.

Workup

  1. temperatureby heating
  2. temperatureunder refluxing for 30 minutes
  3. customThen, the solvent was removed by evaporation
  4. additionWater was added to the residue
  5. extractionfollowed by extraction with ethyl acetate
  6. washThe organic layer was washed with saturated saline
  7. customAfter the solvent was removed by evaporation
  8. customthe residue was crystallized from diethyl ether-hexane

Sources & evidence

ORD record
ord-202290a4615c44c58380737706d7e9a0
Source dataset
uspto-grants-2007_11
Patent number
US07297698B2

Reaction notes

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