Selenium Dioxide → 7-Bromo-2-quinolinecarboxaldehyde

HRID 408104Notes

Reaction equation

HRID 408104 reaction equation
[Se](=O)=[O:2].[Br:4][C:5]1[CH:14]=[C:13]2[C:8]([CH:9]=[CH:10][C:11]([CH3:15])=[N:12]2)=[CH:7][CH:6]=1>O1CCOCC1>[Br:4][C:5]1[CH:14]=[C:13]2[C:8]([CH:9]=[CH:10][C:11]([CH:15]=[O:2])=[N:12]2)=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 24007Selenium DioxideHCID 123328967-Bromo-2-methylquinoline

Product 1

HCID 366880237-Bromo-2-quinolinecarboxaldehydeYield 124.8%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

Selenium dioxide (1.6 g, 14 mmol, 1.3 eq) was suspended in dioxan (50 mL) and was heated to 60° C. At this temperature 7-bromoquinaldine (2.5 g, 11.2 mmol) was introduced and the mixture was left at 80° C. for 3 hours. After cooling the mixture to room temperature, the crude slurry was filtered on celite, eluted with dioxan and concentrated under reduced pressure. The product was obtained pure as a brown solid (3.3 g, >98%) that was used without furter purification.

Workup

  1. temperatureAfter cooling the mixture to room temperature
  2. filtrationthe crude slurry was filtered on celite
  3. washeluted with dioxan
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e538b56964c2423a85a9c806175abb70
Source dataset
uspto-grants-2014_06
Patent number
US08759331B2

Reaction notes

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