Oxalic Acid → 6,7-Dimethyl-2,3-quinoxalinediol

HRID 1857409Notes

Reaction equation

HRID 1857409 reaction equation
[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([NH2:9])=[C:4]([NH2:10])[CH:3]=1.[C:11](O)(=[O:15])[C:12](O)=[O:13]>Cl.O>[CH3:8][C:7]1[CH:6]=[C:5]2[C:4](=[CH:3][C:2]=1[CH3:1])[NH:10][C:12](=[O:13])[C:11](=[O:15])[NH:9]2

Participants

5

Reactant 2

HCID 971Oxalic AcidHCID 766354,5-Dimethyl-1,2-phenylenediamine

Product 1

HCID 2476706,7-Dimethyl-2,3-quinoxalinediolYield 938.5%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

A mixture of 2.72 g (2.0 mmol) of 4,5-dimethyl-1,2-phenylenediamine and 1.92 g (21.3 mmol) of oxalic acid in 30 mL of 2N HCl was refluxed for 2.5 h and cooled to room temperature. The mixture was diluted with 20 mL of H2O, filtered, washed with water, and dried to leave a pale-brown solid 3.57 g (94%); mp>250° C.; 1H NMR (DMSO-d6), 2.161 (s,6), 6.869 (s,2), 11.78 (s,2).

Workup

  1. temperaturewas refluxed for 2.5 h
  2. filtrationfiltered
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-50e15b8796ac400e8f926e6c0205ed10
Source dataset
uspto-grants-2000_11
Patent number
US06147075

Reaction notes

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