Acetonitrile → 5,8-Quinoxalinedione

HRID 1153730Notes

Reaction equation

HRID 1153730 reaction equation
C(#N)C.C[O:5][C:6]1[CH:15]=[CH:14][C:13]([O:16]C)=[C:12]2[C:7]=1[N:8]=[CH:9][CH:10]=[N:11]2>[Ag].O>[N:8]1[C:7]2[C:6](=[O:5])[CH:15]=[CH:14][C:13](=[O:16])[C:12]=2[N:11]=[CH:10][CH:9]=1

Participants

5

Reactant 2

HCID 6342AcetonitrileHCID 600389HCID 600389, compound

Product 1

HCID 113556455,8-Quinoxalinedione

Reagents, catalysts & solvents 2

HCID 23954SilverCatalystHCID 962WaterSolvent

Procedure

A suspension of 22 g. of the silver catalyst prepared above, 148 ml. of acetonitrile, and 32 ml. of water was added over a 30 minute period to 2.0 g. of 5,8-dimethoxyquinoxaline. The reaction was stirred for two hours at room temperature. The catalyst was filtered off and washed with methylene chloride. Water was added to the filtrate and the filtrate was then extracted with the methylene chloride used to wash the catalyst. The methylene chloride was dried over sodium sulfate and evaporated to give the title compound as a brown powder which was used without further purification.

Workup

  1. additionA suspension of 22 g
  2. filtrationThe catalyst was filtered off
  3. washwashed with methylene chloride
  4. additionWater was added to the filtrate
  5. extractionthe filtrate was then extracted with the methylene chloride
  6. washto wash the catalyst
  7. dry with materialThe methylene chloride was dried over sodium sulfate
  8. customevaporated

Sources & evidence

ORD record
ord-93aa2008ddd64c848d300b2f5e0a1fbc
Source dataset
uspto-grants-1984_12
Patent number
US04486432

Reaction notes

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