Selenium Dioxide → 6-Fluoro-8-methoxyquinoline-2-carbaldehyde

HRID 338916Notes

Reaction equation

HRID 338916 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([O:12][CH3:13])[CH:11]=1)[N:8]=[C:7]([CH3:14])[CH:6]=[CH:5]2.[Se](=O)=[O:16]>O1CCOCC1.O>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([O:12][CH3:13])[CH:11]=1)[N:8]=[C:7]([CH:14]=[O:16])[CH:6]=[CH:5]2

Participants

4

Reactant 2

HCID 24007Selenium DioxideHCID 867074466-Fluoro-8-methoxy-2-methylquinoline

Product 1

HCID 867074476-Fluoro-8-methoxyquinoline-2-carbaldehydeYield 78.8%

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

To 6-fluoro-8-methoxy-2-methylquinoline (500 mg, 2.62 mmol) in dioxane/water (5 mL/0.5 mL) at ambient temperature was added selenium dioxide (348 mg, 3.14 mmol) and the reaction was heated to reflux for 2-3 hours. After cooling, the reaction was filtered and the solids were washed with DCM. The filtrate was dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified by reverse phase chromatography (SP4, 25M, eluting with a gradient of water/ACN 100:0 to 0:100, 20 column volumes) to yield 6-fluoro-8-methoxyquinoline-2-carbaldehyde (423 mg, 78.8% yield) as a tan solid.

Workup

  1. temperaturethe reaction was heated
  2. temperatureto reflux for 2-3 hours
  3. temperatureAfter cooling
  4. filtrationthe reaction was filtered
  5. washthe solids were washed with DCM
  6. dry with materialThe filtrate was dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by reverse phase chromatography (SP4, 25M
  10. washeluting with a gradient of water/ACN 100:0 to 0:100, 20 column volumes)

Sources & evidence

ORD record
ord-8bd726af67dd48d0bf7df369a8ad5013
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

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