O-Phenylenediamine → 2,3-Dihydroxyquinoxaline

HRID 1658048Notes

Reaction equation

HRID 1658048 reaction equation
[C:1]1([NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH2:7].[C:9](OCC)(=[O:13])[C:10]([O-])=[O:11]>>[NH:7]1[C:2]2[C:1](=[CH:6][CH:5]=[CH:4][CH:3]=2)[NH:8][C:10](=[O:11])[C:9]1=[O:13]

Participants

3

Reactant 2

HCID 7243O-PhenylenediamineHCID 21943339Ethanedioic acid, monoethyl ester

Product 1

HCID 274912,3-Dihydroxyquinoxaline

Procedure

o-Phenylenediamine (10 grams) and ethyl oxalate (100 ml.) were mixed and the mixture was heated, with stirring, to reflux and refluxed for 30 minutes. The reaction mixture was then cooled and the resulting precipitate, the desired 2(1H), 3(4H)-quinoxalinedione, was separated by filtration. The product did not melt below 400°C. It was recrystallized from a mixture of dimethylformamide and water, yielding a purified product which did not melt below 405°C. The identity of the product was confirmed by NMR and IR. Elemental analysis showed

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux
  3. temperaturerefluxed for 30 minutes
  4. temperatureThe reaction mixture was then cooled
  5. customthe resulting precipitate, the desired 2(1H), 3(4H)-quinoxalinedione, was separated by filtration
  6. customdid not melt below 400°C
  7. customIt was recrystallized from a mixture of dimethylformamide and water
  8. customyielding a purified product which
  9. customdid not melt below 405°C

Sources & evidence

ORD record
ord-2225fd98fc1049a8a7f020a80d261b58
Source dataset
uspto-grants-1976_06
Patent number
US03962440

Reaction notes

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