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

HRID 343795Notes

Reaction equation

HRID 343795 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% solution in methanol, 274 ml, 1.28 mol) was added to a suspension of 5-amino-2,3,6,7-tetrachloroquinoxaline (72.4 g, 0.256 mol) in dry methanol (1 l) and the resulting mixture was heated at 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 solution was dried (MgSO4) and concentrated under reduced pressure. The crude product was purified by trituration with methanol, followed by dissolution in dichloromethane (2 l) and filtration. The filtrate was concentrated under reduced pressure to give 5-amino-6,7-dichloro-2,3-dimethoxy-quinoxaline as a yellow solid (55.0 g, 79%).

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureat 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 solution was dried (MgSO4)
  7. concentrationconcentrated under reduced pressure
  8. customThe crude product was purified by trituration with methanol
  9. dissolutionfollowed by dissolution in dichloromethane (2 l)
  10. filtrationfiltration
  11. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-f88f32b0a8664c0186c19092f7830fc9
Source dataset
uspto-grants-1999_01
Patent number
US05863917

Reaction notes

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