HCID 23284530, compound → (2-Chloropyridin-3-yl)(thiophen-2-yl)methanone

HRID 368978Notes

Reaction equation

HRID 368978 reaction equation
[Cl:1][C:2]1[C:7]([CH:8]([C:10]2[S:11][CH:12]=[CH:13][CH:14]=2)[OH:9])=[CH:6][CH:5]=[CH:4][N:3]=1>[O-2].[O-2].[Mn+4].C1(C)C=CC=CC=1>[Cl:1][C:2]1[C:7]([C:8]([C:10]2[S:11][CH:12]=[CH:13][CH:14]=2)=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 1

HCID 23284530HCID 23284530, compound

Product 1

HCID 15135620(2-Chloropyridin-3-yl)(thiophen-2-yl)methanoneYield 87.5%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 1140TolueneSolvent

Procedure

To a toluene (100 ml) solution of α-(2-chloropyridin-3-yl)-2-thiophenmethanol (6.14 g, 27.2 mmol) was added 85% manganese dioxide (25 g, 245 mmol), followed by 2 hours of heating under reflux. The reaction solution was passed through celite and the resulting filtrate was concentrated under a reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane-chloroform) to give 2-chloro-3-(2-thiophenecarbonyl)pyridine (5.32 g, 23.8 mmol, 87%).

Workup

  1. temperatureof heating
  2. temperatureunder reflux
  3. concentrationthe resulting filtrate was concentrated under a reduced pressure
  4. customThe resulting residue was purified by silica gel column chromatography (hexane-chloroform)

Sources & evidence

ORD record
ord-01a9fbfad991498ea320c464207272c7
Source dataset
uspto-grants-2000_10
Patent number
US06136810

Reaction notes

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