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

HRID 443978Notes

Reaction equation

HRID 443978 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.)
  3. customRecrystallization from methanol-chloroform
  4. customgave fine white needles

Sources & evidence

ORD record
ord-c5d0ecfd9a744dc5bb88cdb958ad0061
Source dataset
uspto-grants-1981_04
Patent number
US04262123

Reaction notes

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