Ethyl pyruvate → 3,6,7-trimethylquinoxalin-2-ol

HRID 2051647Notes

Reaction equation

HRID 2051647 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](OCC)(=[O:15])[C:12]([CH3:14])=O>O1CCCC1>[CH3:14][C:12]1[C:11](=[O:15])[NH:9][C:5]2[C:4]([N:10]=1)=[CH:3][C:2]([CH3:1])=[C:7]([CH3:8])[CH:6]=2

Participants

4

Reactant 2

HCID 12041Ethyl pyruvateHCID 766354,5-Dimethyl-1,2-phenylenediamine

Product 1

HCID 2474893,6,7-trimethylquinoxalin-2-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4,5-Dimethyl-o-phenylenediamine (10.0 g., 0.073 mol.) was dissolved in tetrahydrofuran (200 ml.) and ethyl pyruvate (12.75 g., 0.11 mol.) added. The reaction mixture was stirred at room temperature for eighteen hours, during which time a white solid precipitated was collected by filtration (13.35 g.). Recrystallization from methanol-chloroform gave fine white needles. (12.65 g., m.p. 306-308°, 92%).

Workup

  1. customprecipitated
  2. filtrationwas collected by filtration (13.35 g.)
  3. customRecrystallization from methanol-chloroform
  4. customgave fine white needles

Sources & evidence

ORD record
ord-b7a23e633b0f4040b7a410f536369942
Source dataset
uspto-grants-1980_01
Patent number
US04181724

Reaction notes

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