Selenium Dioxide → 6-Fluoroquinoxaline-2-carbaldehyde

HRID 1826917Notes

Reaction equation

HRID 1826917 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-2acb4121027940cab0e66608d3e905f8
Source dataset
uspto-grants-2006_05
Patent number
US07053104B2

Reaction notes

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