1,4-Dioxane → 6-Bromoquinoline-2-carbaldehyde

HRID 882075Notes

Reaction equation

HRID 882075 reaction equation
[Se].[Br:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[C:8]([CH3:13])[CH:7]=[CH:6]2.[O:14]1CCOCC1>>[Br:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[C:8]([CH:13]=[O:14])[CH:7]=[CH:6]2

Participants

4

Reactant 3

HCID 312751,4-DioxaneHCID 5228856-Bromo-2-methylquinolineHCID 6326970Selenium

Product 1

HCID 183731406-Bromoquinoline-2-carbaldehyde

Procedure

Selenium dioxyde (1.3 g, 12 mmol, 1.3 eq) in suspension in dioxane (50 mL) was heated at 60° C. 6-bromoquinaldine (2 g, 9 mmol) was then introduced and the mixture was left to react at 80° C. for 3 hours. After cooling to room temperature, the mixture was filtered on celite, eluted with dioxane and concentrated under reduced pressure. The product obtained is a pure white solid (3.3 g, >98%).

Workup

  1. waitthe mixture was left
  2. customto react at 80° C. for 3 hours
  3. filtrationthe mixture was filtered on celite
  4. washeluted with dioxane
  5. concentrationconcentrated under reduced pressure
  6. customThe product obtained

Sources & evidence

ORD record
ord-a6db4ca1c81143349985b8b7af71c4f0
Source dataset
uspto-grants-2015_03
Patent number
US08993767B2

Reaction notes

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