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

HRID 1025477Notes

Reaction equation

HRID 1025477 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([NH2:10])[C:5]([NH2:9])=[CH:6][C:7]=1[CH3:8].[C:11](OCC)(=[O:17])[C:12](OCC)=[O:13]>>[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:17])[NH:9]2

Participants

3

Reactant 2

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

Product 1

HCID 2476706,7-Dimethyl-2,3-quinoxalinediol

Procedure

A mixture of 4,5-dimethyl-benzene-1,2-diamine (60 g) and diethyl oxalate (600 mL) was heated under reflux for 1 h and then cooled. The precipitate of 6,7-dimethyl-1,4-dihydro-quinoxaline-2,3-dione was filtered off and washed with 96% ethanol to give 38 g of the title compound. ESI-MS: m/z 191.1 [MH+], 403.3 [2MNa+]; required MW=190.2

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 1 h
  3. temperaturecooled
  4. filtrationThe precipitate of 6,7-dimethyl-1,4-dihydro-quinoxaline-2,3-dione was filtered off
  5. washwashed with 96% ethanol

Sources & evidence

ORD record
ord-05354a1a023b4be983fc3be7f3e8b649
Source dataset
uspto-grants-2014_05
Patent number
US08729082B2

Reaction notes

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