Oxalic Acid → 1,4-Dihydro-6,7-dichloro-5-methyl-quinoxaline-2,3-dione

HRID 1957119Notes

Reaction equation

HRID 1957119 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:3]([CH3:11])=[C:2]2[C:7](=[CH:6][C:5]=1[Cl:9])[NH:8][C:13](=[O:14])[C:12](=[O:16])[NH:1]2

Participants

4

Reactant 2

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

Product 1

HCID 105824891,4-Dihydro-6,7-dichloro-5-methyl-quinoxaline-2,3-dioneYield 66%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A mixture of 2,3-diamino-5,6-dichlorotoluene (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 1,4-dihydro-6,7-dichloro-5-methyl-quinoxaline-2,3-dione (22.06 g, 66%). 1H NMR (300 MHz, DMSO) 2.40 (3H, s), 7.14 (1H, s), 11.37 (1H, s), 11.94 (1H, s).

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-3cda3d871d50449e8b95485a8e066979
Source dataset
uspto-grants-1998_07
Patent number
US05783572

Reaction notes

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