Selenium Dioxide → (R)-6-fluoro-8-(1-methoxypropan-2-yloxy)quinoline-2-carbaldehyde

HRID 338983Notes

Reaction equation

HRID 338983 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([O:12][C@H:13]([CH3:17])[CH2:14][O:15][CH3:16])[CH:11]=1)[N:8]=[C:7]([CH3:18])[CH:6]=[CH:5]2.[Se](=O)=[O:20]>O1CCOCC1.O>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([O:12][C@H:13]([CH3:17])[CH2:14][O:15][CH3:16])[CH:11]=1)[N:8]=[C:7]([CH:18]=[O:20])[CH:6]=[CH:5]2

Participants

5

Reactant 2

HCID 24007Selenium DioxideHCID 86707492(R)-6-fluoro-8-(1-methoxypropan-2-yloxy)-2-methylquinoline

Product 1

HCID 86707493(R)-6-fluoro-8-(1-methoxypropan-2-yloxy)quinoline-2-carbaldehydeYield 89.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of (R)-6-fluoro-8-(1-methoxypropan-2-yloxy)-2-methylquinoline (0.70 g, 2.8 mmol) in dioxane (55 mL) and water (0.55 mL) was added selenium dioxide (0.38 g, 3.4 mmol) and the resultant mixture heated at reflux for 2 hours. The cooled reaction mixture was filtered through a plug of Celite® to remove solids, rinsing with dichloromethane. The filtrate was concentrated under reduced pressure and purified by normal phase chromatography on silica gel (10-30% ethyl acetate/hexanes) to afford the title compound (0.66 g, 89%).

Workup

  1. temperatureat reflux for 2 hours
  2. customThe cooled reaction mixture
  3. filtrationwas filtered through a plug of Celite®
  4. customto remove solids
  5. washrinsing with dichloromethane
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. custompurified by normal phase chromatography on silica gel (10-30% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-3b0bf4944c294a319160acdc8c7e2f24
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

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