Sodium Methoxide → HCID 69243755, compound

HRID 1878290Notes

Reaction equation

HRID 1878290 reaction equation
[NH2:1][C:2]1[C:11](Cl)=[N:10][C:9]2[C:4](=[CH:5][C:6]([CH3:14])=[C:7]([CH3:13])[CH:8]=2)[N:3]=1.[CH3:15][O-:16].[Na+]>O1CCCC1.CO>[NH2:1][C:2]1[C:11]([O:16][CH3:15])=[N:10][C:9]2[C:4](=[CH:5][C:6]([CH3:14])=[C:7]([CH3:13])[CH:8]=2)[N:3]=1

Participants

5

Reactant 2

HCID 10942334Sodium MethoxideHCID 856592133-Chloro-6,7-dimethyl-quinoxalin-2-ylamine

Product 1

HCID 69243755HCID 69243755, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To 2-amino-3-chloro-6,7-dimethyl quinoxaline (2.59 g, 12.5 mmol) dissolved in tetrahydrofuran (40 ml), 25 wt % sodium methoxide (4.05 g, 18.7 mmol) in methanol was added at room temperature and stirred further at room temperature for 1 hour. The resulting mixture was concentrated under the reduced pressure to remove the solvent. The product was extracted with ethyl acetate 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 2.38 g of the titled compound (yield, 94%).

Workup

  1. concentrationThe resulting mixture was concentrated under the reduced pressure
  2. customto remove the solvent
  3. extractionThe product was extracted with ethyl acetate
  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-bd0f29f6a9634438a64656254742baec
Source dataset
uspto-grants-2012_11
Patent number
US08314100B2

Reaction notes

Loading…