Methanol → 5-Amino-6,7-dichloro-2,3-dimethoxyquinoxaline

HRID 842674Notes

Reaction equation

HRID 842674 reaction equation
[CH3:1][O-:2].[Na+].[NH2:4][C:5]1[C:14]([Cl:15])=[C:13]([Cl:16])[CH:12]=[C:11]2[C:6]=1[N:7]=[C:8](Cl)[C:9](Cl)=[N:10]2.[CH3:19][OH:20]>>[NH2:4][C:5]1[C:14]([Cl:15])=[C:13]([Cl:16])[CH:12]=[C:11]2[C:6]=1[N:7]=[C:8]([O:20][CH3:19])[C:9]([O:2][CH3:1])=[N:10]2

Participants

4

Reactant 3

HCID 887MethanolHCID 10844262HCID 10844262, compoundHCID 10942334Sodium Methoxide

Product 1

HCID 106066205-Amino-6,7-dichloro-2,3-dimethoxyquinoxalineYield 79%

Procedure

A solution of sodium methoxide (25% w/w solution in methanol, 274 mL, 1.28 mmol) was added to a suspension of 5-amino-2,3,6,7-tetrachloroquinoxaline (72.4 g, 0.256 mmol) in dry methanol (1 L) and the resulting mixture was heated under reflux for 30 minutes. The mixture was cooled, concentrated under reduced pressure, and the residue partitioned between water and ethyl acetate (total of 8 L). The organic extracts were dried (MgSO4) and concentrated under reduced pressure. The crude product was triturated with methanol then dissolved in dichloromethane (2 L) and filtered. The filtrate was concentrated under reduced pressure to give the title compound as a yellow solid (55.0 g, 79%).

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 30 minutes
  3. temperatureThe mixture was cooled
  4. concentrationconcentrated under reduced pressure
  5. customthe residue partitioned between water and ethyl acetate (total of 8 L)
  6. dry with materialThe organic extracts were dried (MgSO4)
  7. concentrationconcentrated under reduced pressure
  8. customThe crude product was triturated with methanol
  9. dissolutionthen dissolved in dichloromethane (2 L)
  10. filtrationfiltered
  11. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-5e76b160c24a40419d3c38b9e2d47cdc
Source dataset
uspto-grants-2002_04
Patent number
US06376490B1

Reaction notes

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