Sodium Methoxide → 2-Amino-3,6,7-trimethoxyquinoxaline

HRID 1878298Notes

Reaction equation

HRID 1878298 reaction equation
[NH2:1][C:2]1[C:11](Cl)=[N:10][C:9]2[C:4](=[CH:5][C:6]([O:15][CH3:16])=[C:7]([O:13][CH3:14])[CH:8]=2)[N:3]=1.[CH3:17][O-:18].[Na+]>O1CCCC1.CO>[NH2:1][C:2]1[C:11]([O:18][CH3:17])=[N:10][C:9]2[C:4](=[CH:5][C:6]([O:15][CH3:16])=[C:7]([O:13][CH3:14])[CH:8]=2)[N:3]=1

Participants

5

Reactant 2

HCID 10942334Sodium MethoxideHCID 866257813-Chloro-6,7-dimethoxyquinoxalin-2-amine

Product 1

HCID 692443442-Amino-3,6,7-trimethoxyquinoxalineYield 85.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To 2-amino-3-chloro-6,7-dimethoxyquinoxaline (3.27 g, 13.6 mmol) dissolved in tetrahydrofuran (40 ml), 25 wt % sodium methoxide (4.41 g, 20.4 mmol) in methanol was added at room temperature and stirred further at room temperature for 2 hour. 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 a n-hexane:ethyl acetate (2:1) mixture and concentration gave 2.73 g of the titled compound (yield, 85%).

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 a n-hexane:ethyl acetate (2:1) mixture and concentration

Sources & evidence

ORD record
ord-d483440e25414c13bc3909b2443f496b
Source dataset
uspto-grants-2012_11
Patent number
US08314100B2

Reaction notes

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