1,4-Dioxane → 7-Bromo-2-quinolinecarboxaldehyde

HRID 882076Notes

Reaction equation

HRID 882076 reaction equation
[Se].[Br:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][C:9]([CH3:13])=[N:10]2)=[CH:5][CH:4]=1.[O:14]1CCOCC1>>[Br:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][C:9]([CH:13]=[O:14])=[N:10]2)=[CH:5][CH:4]=1

Participants

4

Reactant 3

HCID 312751,4-DioxaneHCID 6326970SeleniumHCID 123328967-Bromo-2-methylquinoline

Product 1

HCID 366880237-Bromo-2-quinolinecarboxaldehydeYield 98%

Procedure

Selenium dioxyde (1.6 g, 14 mmol, 1.3 eq) in suspension in dioxane (50 mL) was heated at 60° C. 7-bromoquinaldine (2.5 g, 11.2 mmol) was the 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 was obtained pure as a white solid (3.3 g, >98%).

Workup

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

Sources & evidence

ORD record
ord-8bdc91348055448b914ca62325e11728
Source dataset
uspto-grants-2015_03
Patent number
US08993767B2

Reaction notes

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