Sodium Methoxide → HCID 66918098, compound

HRID 1878161Notes

Reaction equation

HRID 1878161 reaction equation
[NH2:1][C:2]1[C:3](Cl)=[N:4][C:5]2[C:10]([N:11]=1)=[CH:9][C:8]([O:12][CH3:13])=[CH:7][CH:6]=2.[CH3:15][O-:16].[Na+]>O1CCCC1.CO>[NH2:1][C:2]1[C:3]([O:16][CH3:15])=[N:4][C:5]2[C:10]([N:11]=1)=[CH:9][C:8]([O:12][CH3:13])=[CH:7][CH:6]=2

Participants

5

Reactant 2

HCID 10942334Sodium MethoxideHCID 866257783-Amino-2-chloro-6-methoxyquinoxaline

Product 1

HCID 66918098HCID 66918098, compoundYield 80.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To 3-amino-2-chloro-6-methoxyquinoxaline (1.50 g, 7.16 mmol) dissolved in tetrahydrofuran (60 ml), 25 wt % sodium methoxide (15.5 g, 71.6 mmol) in methanol was added at room temperature and stirred further at room temperature for 21 hours. 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 1.18 g of the titled compound (yield, 80%).

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-d7bae9c15b744566812b2370261a0eed
Source dataset
uspto-grants-2012_11
Patent number
US08314100B2

Reaction notes

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