Selenium Dioxide → 6-Fluoro-8-(3-methoxypropoxy)quinoline-2-carbaldehyde

HRID 339045Notes

Reaction equation

HRID 339045 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([O:12][CH2:13][CH2:14][CH2:15][O:16][CH3:17])[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][CH2:13][CH2:14][CH2:15][O:16][CH3:17])[CH:11]=1)[N:8]=[C:7]([CH:18]=[O:20])[CH:6]=[CH:5]2

Participants

5

Reactant 2

HCID 24007Selenium DioxideHCID 709832516-Fluoro-8-(3-methoxypropoxy)-2-methylquinoline

Product 1

HCID 867075356-Fluoro-8-(3-methoxypropoxy)quinoline-2-carbaldehydeYield 89%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 6-fluoro-8-(3-methoxypropoxy)-2-methylquinoline (0.22 g, 0.87 mmol) in dioxane (20 mL) and water (0.2 mL) was added selenium dioxide (0.12 g, 1.0 mmol) and the resultant mixture was heated at reflux for 5 hours. The cooled reaction mixture was filtered through a plug of Celite®, washing the solids with dichloromethane. The filtrate was concentrated under reduced pressure and the residue was purified by normal phase chromatography on silica gel (10-30% ethyl acetate/hexanes) to provide the title compound (0.20 g, 89%).

Workup

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

Sources & evidence

ORD record
ord-9414dcebc12a41459ad29a5183fb62b1
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

Loading…