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

HRID 338887Notes

Reaction equation

HRID 338887 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([O:12][CH:13]([CH3:15])[CH3:14])[CH:11]=1)[N:8]=[C:7]([CH3:16])[CH:6]=[CH:5]2.[Se](=O)=[O:18]>O1CCOCC1.O>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([O:12][CH:13]([CH3:14])[CH3:15])[CH:11]=1)[N:8]=[C:7]([CH:16]=[O:18])[CH:6]=[CH:5]2

Participants

4

Reactant 2

HCID 24007Selenium DioxideHCID 709829066-Fluoro-8-isopropoxy-2-methylquinoline

Product 1

HCID 867074316-Fluoro-8-isopropoxyquinoline-2-carbaldehydeYield 35%

Reagents, catalysts & solvents 1

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

Procedure

To 6-fluoro-8-isopropoxy-2-methylquinoline (1.1 g, 5.02 mmol) in dioxane/water (3.5 ml/0.3 mL) at ambient temperature was added selenium dioxide (0.668 g, 6.02 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 crude material 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-isopropoxyquinoline-2-carbaldehyde (410 mg, 35.0% 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 crude material 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-40f0da90c54746e996ccfd8a355ae76b
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

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