Methanol → 5-Amino-6,7-dichloro-2,3-dimethoxyquinoxaline
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]2Participants
4
Procedure
A solution of sodium methoxide (25% w/w 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 liter) 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 liters). The organic extracts were dried (MgSO4) and concentrated under reduced pressure. The crude product was triturated with methanol then dissolved in dichloromethane (2 liters) and filtered. The filtrate was concentrated under reduced pressure to give the title compound as a yellow solid (55.0 g, 79%).
Workup
- temperaturethe resulting mixture was heated
- temperatureunder reflux for 30 minutes
- temperatureThe mixture was cooled
- concentrationconcentrated under reduced pressure
- customthe residue partitioned between water and ethyl acetate (total of 8 liters)
- dry with materialThe organic extracts were dried (MgSO4)
- concentrationconcentrated under reduced pressure
- customThe crude product was triturated with methanol
- dissolutionthen dissolved in dichloromethane (2 liters)
- filtrationfiltered
- concentrationThe filtrate was concentrated under reduced pressure
Sources & evidence
- ORD record
- ord-b7770651432541f3b88a249d7c69f035
- Source dataset
- uspto-grants-2001_12
- Patent number
- US06333326B1
Reaction notes
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