Oxalic Acid → 6,7-Dichloro-5-methyl-quinoxalin-2,3-dione

HRID 1458591Notes

Reaction equation

HRID 1458591 reaction equation
[NH2:1][C:2]1[C:7]([NH2:8])=[CH:6][C:5]([Cl:9])=[C:4]([Cl:10])[C:3]=1[CH3:11].[C:12](O)(=[O:16])[C:13](O)=[O:14]>Cl>[Cl:10][C:4]1[C:5]([Cl:9])=[CH:6][C:7]2[C:2](=[N:1][C:12](=[O:16])[C:13](=[O:14])[N:8]=2)[C:3]=1[CH3:11]

Participants

4

Reactant 2

HCID 971Oxalic AcidHCID 106077272,3-Diamino-5,6-dichlorotoluene

Product 1

HCID 220969936,7-Dichloro-5-methyl-quinoxalin-2,3-dioneYield 66.3%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A mixture of 2,3-diamino-5,6-dichlorotoluene (from step (c), 21.6 g, 0.137 mol) and oxalic acid (18.45 g, 0.206 mol) in hydrochloric acid (4M, 900 ml) was heated at reflux for 6 hours, cooled and filtered. The dark brown solid was suspended in diethyl ether, filtered and washed with more ether to give 6,7-dichloro-5-methyl-quinoxalin-2,3-dione (22.06 g, 66%).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 6 hours
  3. temperaturecooled
  4. filtrationfiltered
  5. filtrationfiltered
  6. washwashed with more ether

Sources & evidence

ORD record
ord-1b0eb02bf46947e5a92f3ba1ccdc77c7
Source dataset
uspto-grants-1998_12
Patent number
US05852016

Reaction notes

Loading…