Methylglyoxal → 2-Methyl-8-nitroquinoxaline

HRID 1883181Notes

Reaction equation

HRID 1883181 reaction equation
[N+:1]([C:4]1[C:5]([NH2:11])=[C:6]([NH2:10])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[CH3:12][C:13]([CH:15]=O)=O.O>C(O)C>[CH3:15][C:13]1[CH:12]=[N:10][C:6]2[C:5](=[C:4]([N+:1]([O-:3])=[O:2])[CH:9]=[CH:8][CH:7]=2)[N:11]=1

Participants

5

Reactant 3

HCID 880MethylglyoxalHCID 962WaterHCID 43595253-Nitro-1,2-phenylenediamine

Product 1

HCID 235104162-Methyl-8-nitroquinoxalineYield 67.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 3-nitro-1,2-phenylenediamine (5.02 g) in ethanol (500 mL) was added at 60° C. a 40% aqueous solution of pyruvic aldehyde (17.72 g). The reaction solution was refluxed for 10 minutes, and thereto was added water (300 mL). The mixture was cooled to room temperature, and concentrated under reduced pressure. The precipitated crystals were collected by filtration, washed with cold water, and dried under reduced pressure to give 2-methyl-8-nitroquinoxaline (4.17 g, 67%) as orange crystals.

Workup

  1. temperatureThe reaction solution was refluxed for 10 minutes
  2. concentrationconcentrated under reduced pressure
  3. filtrationThe precipitated crystals were collected by filtration
  4. washwashed with cold water
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-04e6af435934445eb469f71aa2c1b6ed
Source dataset
uspto-grants-2004_07
Patent number
US06759429B2

Reaction notes

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