1,4-Dioxane → 3-Fluoro-7-(2-methoxyethoxy)quinoline-2-carbaldehyde

HRID 339096Notes

Reaction equation

HRID 339096 reaction equation
[F:1][C:2]1[C:3]([CH3:17])=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[C:7]([O:12][CH2:13][CH2:14][O:15][CH3:16])[CH:6]=2.[O:18]1CCOCC1>O>[F:1][C:2]1[C:3]([CH:17]=[O:18])=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[C:7]([O:12][CH2:13][CH2:14][O:15][CH3:16])[CH:6]=2

Participants

4

Reactant 2

HCID 312751,4-DioxaneHCID 709835103-Fluoro-7-(2-methoxyethoxy)-2-methylquinoline

Product 1

HCID 867075593-Fluoro-7-(2-methoxyethoxy)quinoline-2-carbaldehydeYield 97%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 3-fluoro-7-(2-methoxyethoxy)-2-methylquinoline (0.234 g, 0.995 mmol) and SeO2 (0.132 g, 1.19 mmol) in dioxane (10 mL) and water (0.1 mL) was stirred at 102° C. (bath) for 5 hours. The solid was removed by filtration. The filtrated was concentrated under reduced pressure. The residue obtained was purified by flash chromatography (1:1 hexane/ethyl acetate) to give 3-fluoro-7-(2-methoxyethoxy)quinoline-2-carbaldehyde (0.24 g, 0.963 mmol, 97% yield) as a solid.

Workup

  1. customThe solid was removed by filtration
  2. concentrationThe filtrated was concentrated under reduced pressure
  3. customThe residue obtained
  4. customwas purified by flash chromatography (1:1 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-4a32f34fe13f47269c111366a4e01618
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

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