Methylglyoxal → 2-Methyl-6-fluoroquinoxaline

HRID 1189192Notes

Reaction equation

HRID 1189192 reaction equation
O=[C:2]([CH3:5])[CH:3]=O.[F:6][C:7]1[CH:8]=[C:9]([NH2:14])[C:10]([NH2:13])=[CH:11][CH:12]=1>O>[F:6][C:7]1[CH:8]=[C:9]2[C:10](=[CH:11][CH:12]=1)[N:13]=[C:2]([CH3:5])[CH:3]=[N:14]2

Participants

4

Reactant 2

HCID 880MethylglyoxalHCID 1645844-Fluorobenzene-1,2-diamine

Product 1

HCID 133808502-Methyl-6-fluoroquinoxalineYield 80%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A solution of 2-oxo-propionaldehyde (0.19 mL, 1.20 mmol) and 4-fluoro-benzene-1,2-diamine (150 mg, 1.19 mmol) in water (1.3 mL) was placed in a microwave tube and heated for 1 min. at 150 W. Then the reaction mixture was diluted with water and extracted twice with AcOEt. The organic phase was washed with water, brine, dried over MgSO4, filtered and evaporated. The crude residue was purified by flash chromatography (cyclohexane/AcOEt 4:1) to yield 154 mg (0.95 mmol, 80%) of 6-fluoro-2-methyl-quinoxaline.

Workup

  1. temperatureheated for 1 min. at 150 W
  2. extractionextracted twice with AcOEt
  3. washThe organic phase was washed with water, brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude residue was purified by flash chromatography (cyclohexane/AcOEt 4:1)

Sources & evidence

ORD record
ord-1688e76b73fe45bfa8c06307a6cc6c20
Source dataset
uspto-grants-2014_03
Patent number
US08674106B2

Reaction notes

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