Selenium Dioxide → 4-(3-Chloropyridin-2-yl)benzaldehyde

HRID 578593Notes

Reaction equation

HRID 578593 reaction equation
[Cl:1][C:2]1[C:3]([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=2)=[N:4][CH:5]=[CH:6][CH:7]=1.[Se](=O)=[O:16]>O1CCOCC1>[Cl:1][C:2]1[C:3]([C:8]2[CH:13]=[CH:12][C:11]([CH:14]=[O:16])=[CH:10][CH:9]=2)=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 24007Selenium DioxideHCID 207099363-Chloro-2-(p-tolyl)pyridine

Product 1

HCID 534262384-(3-Chloropyridin-2-yl)benzaldehydeYield 85%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
25 °C

Procedure

100 g (0.49 mol) of 3-chloro-2-para-tolylpyridine was dissolved in 1 L of 1,4-dioxane in a reactor. 163.4 g (1.47 mol) of selenium dioxide was added, and the mixture was refluxed for 4˜6 hours. The reaction solution was cooled to 25° C., and floating matter was filtered off with celite. A 10% sodium bicarbonate solution was added, and the mixture was extracted with ethyl acetate. The organic layer was dried with magnesium sulfate and concentrated under reduced pressure, yielding 4-(3-chloropyridin-2-yl)benzaldehyde as represented below in a 85% yield.

Workup

  1. temperaturethe mixture was refluxed for 4˜6 hours
  2. filtrationwas filtered off with celite
  3. additionA 10% sodium bicarbonate solution was added
  4. extractionthe mixture was extracted with ethyl acetate
  5. dry with materialThe organic layer was dried with magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9d72973adc8b4788893c4d0b0397c29a
Source dataset
uspto-grants-2015_05
Patent number
US09040572B2

Reaction notes

Loading…