1,4-Dioxane → (S)-6-fluoro-7-(2-methoxypropoxy)quinoline-2-carbaldehyde

HRID 339087Notes

Reaction equation

HRID 339087 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][CH2:13][C@@H:14]([O:16][CH3:17])[CH3:15])[N:8]=[C:7]([CH3:18])[CH:6]=[CH:5]2.[O:19]1CCOCC1>O>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][CH2:13][C@@H:14]([O:16][CH3:17])[CH3:15])[N:8]=[C:7]([CH:18]=[O:19])[CH:6]=[CH:5]2

Participants

4

Reactant 2

HCID 312751,4-DioxaneHCID 70983212(S)-6-fluoro-7-(2-methoxypropoxy)-2-methylquinoline

Product 1

HCID 86707557(S)-6-fluoro-7-(2-methoxypropoxy)quinoline-2-carbaldehydeYield 85%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of crude (S)-6-fluoro-7-(2-methoxypropoxy)-2-methylquinoline (0.281 g, 1.13 mmol) in dioxane (4 mL) and water (0.04 mL) was added SeO2 (0.138 g, 1.24 mmol). The reaction mixture was heated at reflux for 3 hours. After cooling, the mixture was filtered through Celite®. The filtrate was concentrated. The residue was purified by flash chromatography on silica gel (hexanes:EtOAc, 4:1) to give (S)-6-fluoro-7-(2-methoxypropoxy)quinoline-2-carbaldehyde (0.251 g, 85% for two steps) as a solid.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 3 hours
  3. temperatureAfter cooling
  4. filtrationthe mixture was filtered through Celite®
  5. concentrationThe filtrate was concentrated
  6. customThe residue was purified by flash chromatography on silica gel (hexanes:EtOAc, 4:1)

Sources & evidence

ORD record
ord-ee04266c3f114758a5e5edd6c0561f88
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

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