Diethyl Oxalate → 6,7-Dimethyl-2,3-quinoxalinediol

HRID 1186451Notes

Reaction equation

HRID 1186451 reaction equation
[C:1]([O:8]CC)(=O)[C:2]([O:4]CC)=O.[CH3:11][C:12]1[C:17]([CH3:18])=[CH:16][C:15]([NH2:19])=[C:14]([NH2:20])[CH:13]=1>FC(F)(F)S([O-])(=O)=O.[Yb+3].FC(F)(F)S([O-])(=O)=O.FC(F)(F)S([O-])(=O)=O.O>[CH3:18][C:17]1[CH:16]=[C:15]2[C:14](=[CH:13][C:12]=1[CH3:11])[NH:20][C:1](=[O:8])[C:2](=[O:4])[NH:19]2

Participants

5

Reactant 2

HCID 7268Diethyl OxalateHCID 766354,5-Dimethyl-1,2-phenylenediamine

Product 1

HCID 2476706,7-Dimethyl-2,3-quinoxalinediolYield 87%

Reagents, catalysts & solvents 2

HCID 2733225Ytterbium triflateCatalystHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

Diethyl oxalate (4.0 mL, 29 mmol) and ytterbium trifluoromethanesulfonate (226 mg, 0.37 mmol) were added to 4,5-dimethyl-1,2-phenylenediamine (1.0 g, 7.3 mmol) and the mixture was stirred at 80° C. for 2 hours. After water was added to the reaction mixture, the precipitate was washed with ethanol. Thus, 6,7-dimethylquinoxaline-2,3(1H,4H)-dione (1.2 g, yield: 87%) was obtained.

Workup

  1. washthe precipitate was washed with ethanol

Sources & evidence

ORD record
ord-e5aec0d5168e47f5b2dd77597cd737b8
Source dataset
uspto-grants-2014_03
Patent number
US08673908B2

Reaction notes

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