Selenium Dioxide → 6-Fluoro-7-isopropoxyquinoline-2-carbaldehyde

HRID 338931Notes

Reaction equation

HRID 338931 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][CH:13]([CH3:15])[CH3:14])[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](=[CH:10][C:11]=1[O:12][CH:13]([CH3:14])[CH3:15])[N:8]=[C:7]([CH:16]=[O:18])[CH:6]=[CH:5]2

Participants

4

Reactant 2

HCID 24007Selenium DioxideHCID 709833366-Fluoro-7-isopropoxy-2-methylquinoline

Product 1

HCID 867074576-Fluoro-7-isopropoxyquinoline-2-carbaldehyde

Reagents, catalysts & solvents 1

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

Procedure

To 6-fluoro-7-isopropoxy-2-methylquinoline (270 mg, 1.23 mmol) in dioxane/water (5 mL/0.05 mL) was added selenium dioxide (164 mg, 1.48 mmol) and the reaction was heated to reflux for 2 hours. After cooling and concentrating, the residue was purified by chromatography (SP4, 25M, eluting with a gradient of water/ACN 100:0 to 0:100, 20 column volumes) to yield 6-fluoro-7-isopropoxyquinoline-2-carbaldehyde as a solid.

Workup

  1. temperaturethe reaction was heated
  2. temperatureto reflux for 2 hours
  3. temperatureAfter cooling
  4. concentrationconcentrating
  5. customthe residue was purified by chromatography (SP4, 25M
  6. washeluting with a gradient of water/ACN 100:0 to 0:100, 20 column volumes)

Sources & evidence

ORD record
ord-9d0a87fad6bd4a9b870dc40e615c0719
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

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