Sodium Methoxide → HCID 66918137, compound

HRID 1878140Notes

Reaction equation

HRID 1878140 reaction equation
[NH2:1][C:2]1[C:3](Cl)=[N:4][C:5]2[C:10]([N:11]=1)=[CH:9][C:8]([CH3:12])=[CH:7][CH:6]=2.[CH3:14][O-:15].[Na+]>O1CCCC1.CO>[NH2:1][C:2]1[C:3]([O:15][CH3:14])=[N:4][C:5]2[C:10]([N:11]=1)=[CH:9][C:8]([CH3:12])=[CH:7][CH:6]=2

Participants

5

Reactant 2

HCID 10942334Sodium MethoxideHCID 86625777HCID 86625777, compound

Product 1

HCID 66918137HCID 66918137, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To 3-amino-2-chloro-6-methylquinoxaline (550 mg, 2.84 mmol) dissolved in tetrahydrofuran (30 ml), 25 wt % sodium methoxide (6.14 g, 28.4 mmol) in methanol was added at room temperature and stirred further at room temperature for 60 minutes. The resulting mixture was concentrated under the reduced pressure to remove the solvent. The product was extracted with dichloromethane and the organic layer was washed with water and dried over MgSO4. After concentration under the reduced pressure, the crude product was purified by SiO2 column chromatography. Extraction of the residue with n-hexane:ethyl acetate (2:1) mixture and concentration gave 467 mg of the titled compound (yield, 87%).

Workup

  1. concentrationThe resulting mixture was concentrated under the reduced pressure
  2. customto remove the solvent
  3. extractionThe product was extracted with dichloromethane
  4. washthe organic layer was washed with water
  5. dry with materialdried over MgSO4
  6. concentrationAfter concentration under the reduced pressure
  7. customthe crude product was purified by SiO2 column chromatography
  8. extractionExtraction of the residue
  9. concentrationwith n-hexane:ethyl acetate (2:1) mixture and concentration

Sources & evidence

ORD record
ord-cd4c13951485434c975fd0a9cdca28da
Source dataset
uspto-grants-2012_11
Patent number
US08314100B2

Reaction notes

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