Selenium Dioxide → 6-Fluoroquinoxaline-2-carbaldehyde

HRID 2302073Notes

Reaction equation

HRID 2302073 reaction equation
[CH3:1][C:2]1[CH:11]=[N:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([F:12])[CH:8]=2)[N:3]=1.[Se](=O)=[O:14]>C(OCC)(=O)C>[F:12][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[N:3]=[C:2]([CH:1]=[O:14])[CH:11]=[N:10]2

Participants

4

Reactant 2

HCID 24007Selenium DioxideHCID 133808502-Methyl-6-fluoroquinoxaline

Product 1

HCID 221364416-Fluoroquinoxaline-2-carbaldehydeYield 29%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Using the method of Kepez (Monatahefte fur Chemie, 1989, 120, 127-130), a solution of 2-methyl-6-fluoroquinoxaline (225 mg 1.39 mmol) in ethyl acetate (30 mL) was treated with selenium dioxide (2.5 g) and the reaction mixture heated at reflux for 36 hours. The reaction was filtered hot and concentrated. Chromatography through a Biotage silica cartridge (8×4 cm i.d.) using a gradient of hexane to 10% ethyl acetate (in hexane) afforded 71 mg (29%) of 6-fluoroquinoxaline-2-carboxaldehyde.

Workup

  1. temperaturethe reaction mixture heated
  2. temperatureat reflux for 36 hours
  3. filtrationThe reaction was filtered hot
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-a6bdfb92793b42bd89cb82be23e9653e
Source dataset
uspto-grants-2002_08
Patent number
US06429207B1

Reaction notes

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