Methylglyoxal → HCID 824610, compound

HRID 1883186Notes

Reaction equation

HRID 1883186 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[C:6]([NH2:11])[CH:5]=1)([O-:3])=[O:2].[CH3:12][C:13]([CH:15]=O)=O>O>[CH3:15][C:13]1[CH:12]=[N:11][C:6]2[C:7](=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[N:10]=1

Participants

4

Reactant 2

HCID 880MethylglyoxalHCID 51117914-Nitro-1,2-phenylenediamine

Product 1

HCID 824610HCID 824610, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
80 °C

Procedure

To a suspension of 4-nitro-1,2-phenylenediamine (10.0 g) in water (150 mL) was added dropwise a 40% aqueous solution of pyruvic aldehyde (11.76 g) at room temperature. The reaction solution was stirred at 80° C. for 4 hours, and cooled to room temperature. Water (200 mL) was added to the mixture, and the mixture was extracted with chloroform (150 mL×3). The organic layers were combined, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The residual solid was recrystallized from ethanol, collected by filtration, and dried to give 2-methyl-6-nitroquinoxaline (7.38 g, 60%) as red solid.

Workup

  1. temperaturecooled to room temperature
  2. extractionthe mixture was extracted with chloroform (150 mL×3)
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residual solid was recrystallized from ethanol
  7. filtrationcollected by filtration
  8. customdried

Sources & evidence

ORD record
ord-44b6a759491a4225b53997de669fd402
Source dataset
uspto-grants-2004_07
Patent number
US06759429B2

Reaction notes

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