Methanol → 6,7-Dichloro-2,3-dimethoxyquinoxaline

HRID 842700Notes

Reaction equation

HRID 842700 reaction equation
[CH3:1][O-:2].[Na+].Cl[C:5]1[C:14](Cl)=[N:13][C:12]2[C:7](=[CH:8][C:9]([Cl:17])=[C:10]([Cl:16])[CH:11]=2)[N:6]=1.[OH2:18].[CH3:19]O>>[Cl:17][C:9]1[CH:8]=[C:7]2[C:12](=[CH:11][C:10]=1[Cl:16])[N:13]=[C:14]([O:2][CH3:1])[C:5]([O:18][CH3:19])=[N:6]2

Participants

5

Reactant 4

HCID 887Methanol2×HCID 962WaterHCID 40971682,3,6,7-TetrachloroquinoxalineHCID 10942334Sodium Methoxide

Product 1

HCID 120471106,7-Dichloro-2,3-dimethoxyquinoxalineYield 94%

Procedure

A 25% w/w solution of sodium methoxide in methanol (700 ml, 5.15 mmol) was added to a suspension of 2,3,6,7-tetrachloroquinoxaline (175 g, 0.653 mol) in methanol (1.4 L) at the reflux temperature and the mixture was maintained at the reflux temperature for 4 hours. The mixture was cooled and water (2.1 L) added. The slurry was filtered, the solid was washed with water (0.35 L) and isopropanol (0.175 L) to give 6,7-dichloro-2,3-dimethoxyquinoxaline (159 g, 94%) as a beige solid, m.p. 146-148° C.

Workup

  1. temperaturethe mixture was maintained at the reflux temperature for 4 hours
  2. temperatureThe mixture was cooled
  3. filtrationThe slurry was filtered
  4. washthe solid was washed with water (0.35 L) and isopropanol (0.175 L)

Sources & evidence

ORD record
ord-a89bd2db0bf64ef0a84015e7f77f885f
Source dataset
uspto-grants-2002_04
Patent number
US06376490B1

Reaction notes

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