Glyoxylic Acid → 6,7-Dichloroquinoxalin-2(1H)-one

HRID 1614156Notes

Reaction equation

HRID 1614156 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([NH2:9])=[C:4]([NH2:10])[CH:3]=1.[C:11](O)(=O)[CH:12]=[O:13]>CCO>[Cl:1][C:2]1[CH:3]=[C:4]2[C:5](=[CH:6][C:7]=1[Cl:8])[NH:9][C:12](=[O:13])[CH:11]=[N:10]2

Participants

4

Reactant 2

HCID 760Glyoxylic AcidHCID 792974,5-Dichloro-1,2-phenylenediamine

Product 1

HCID 144236366,7-Dichloroquinoxalin-2(1H)-oneYield 90.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4,5-Dichloro-1,2-phenylenediamine (25 g, 141.2 mmol) was suspended in 780 ml EtOH, and 13 g (142.0 mmol) of glyoxylic acid (HO2CCOH/H2O) was added. The mixture was heated at reflux for 3 hours, and then cooled and filtered, yielding 27.45 g of 6,7-dichloroquinoxalin-2-one as a solid. The product (25 g, 116.3 mmol) and 230 ml (911.7 mmol) of phosphorous oxychloride (POCl3) were stirred at reflux (100° C.) for 3 hours. The mixture was cooled and ice/H2O added. The resulting brown/grey solid was filtered, and dried in an oven, yielding approximately 25 g of 2,6,7-trichloroquinoxaline.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 3 hours
  3. temperaturecooled
  4. filtrationfiltered

Sources & evidence

ORD record
ord-0bfab91632c949c2b6864b272605ef2e
Source dataset
uspto-grants-1993_03
Patent number
US05196421

Reaction notes

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