Diethyl Oxalate → HCID 14423648, compound

HRID 1186453Notes

Reaction equation

HRID 1186453 reaction equation
[C:1]([O:8]CC)(=O)[C:2]([O:4]CC)=O.[NH2:11][C:12]1[C:17]([NH2:18])=[CH:16][CH:15]=[CH:14][C:13]=1[CH3:19]>FC(F)(F)S([O-])(=O)=O.[Yb+3].FC(F)(F)S([O-])(=O)=O.FC(F)(F)S([O-])(=O)=O.O>[CH3:19][C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[C:12]=1[NH:11][C:2](=[O:4])[C:1](=[O:8])[NH:18]2

Participants

5

Reactant 2

HCID 7268Diethyl OxalateHCID 175932,3-Diaminotoluene

Product 1

HCID 14423648HCID 14423648, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 2733225Ytterbium triflateCatalystHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

According to Step 1 of Reference Example 10-3, diethyl oxalate (4.5 mL, 33 mmol) and ytterbium trifluoromethanesulfonate (254 mg, 0.41 mmol) were added to 2,3-diaminotoluene (1.0 g, 8.2 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, 5-methylquinoxaline-2,3(1H,4H)-dione (1.1 g, yield: 78%) was obtained.

Workup

  1. washthe precipitate was washed with ethanol

Sources & evidence

ORD record
ord-b5bfe6c6bcd9485c8850d18e7b4012c4
Source dataset
uspto-grants-2014_03
Patent number
US08673908B2

Reaction notes

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