Methylglyoxal → 2-Methyl-6-fluoroquinoxaline

HRID 422385Notes

Reaction equation

HRID 422385 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-62208cdc0e014334bcc4ee0a817468e1
Source dataset
uspto-grants-2012_01
Patent number
US08101637B2

Reaction notes

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