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

HRID 1733455Notes

Reaction equation

HRID 1733455 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 and 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.) Recrystallization from methanol-chloroform
  3. customgave fine white needles

Sources & evidence

ORD record
ord-38f49359dea04660ace0d626f52449ac
Source dataset
uspto-grants-1980_12
Patent number
US04242342

Reaction notes

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