Glyoxal → 6-Methylquinoxaline

HRID 491416Notes

Reaction equation

HRID 491416 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[C:4]([NH2:9])[CH:3]=1.[CH:10]([CH:12]=O)=O>CO>[CH3:1][C:2]1[CH:3]=[C:4]2[C:5](=[CH:6][CH:7]=1)[N:8]=[CH:12][CH:10]=[N:9]2

Participants

4

Reactant 2

HCID 7860GlyoxalHCID 103323,4-Diaminotoluene

Product 1

HCID 2425676-MethylquinoxalineYield 25%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 4-methyl-1,2-phenylenediamine (5.0 g, 41 mmol) in methanol (250 mL) was treated with a solution of 40% aqueous glyoxal and stirred for 16 h. The solvent was evaporated and the residue was distilled under vacuum (2 mm Hg, 85-88° C.) to leave a colorless oil (1.5 g, 25%). LC/MS Method A, r.t.=1.02 mins., purity=99.5%.

Workup

  1. customThe solvent was evaporated
  2. distillationthe residue was distilled under vacuum (2 mm Hg, 85-88° C.)

Sources & evidence

ORD record
ord-7da68beb1f3c456b8e545c555ebb5b90
Source dataset
uspto-grants-2009_05
Patent number
US07531542B2

Reaction notes

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