(6-Iodopyridin-3-yl)methanol → 6-Iodopyridine-3-carbaldehyde

HRID 2426334Notes

Reaction equation

HRID 2426334 reaction equation
[I:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][OH:9])=[CH:4][CH:3]=1>ClCCl.[O-2].[O-2].[Mn+4]>[I:1][C:2]1[N:7]=[CH:6][C:5]([CH:8]=[O:9])=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 23039516(6-Iodopyridin-3-yl)methanol

Product 1

HCID 534852236-Iodopyridine-3-carbaldehyde

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent2×

Procedure

63 g (723 mmol) of manganese dioxide are added to a solution of 17 g (72 mmol) of (6-iodopyrid-3-yl)methanol in 600 ml of dichloromethane. The reaction medium is stirred at room temperature for 20 hours and then filtered through Celite. The precipitate is washed thoroughly with water and the filtrate is evaporated under vacuum. The residue obtained is taken up in dichloromethane and the insoluble material is again filtered off. After evaporation of the filtrate, 13.2 g (78%) of 6-iodopyridine-3-carbaldehyde are obtained in the form of a pale yellow solid with a melting point of 141° C.

Workup

  1. filtrationfiltered through Celite
  2. washThe precipitate is washed thoroughly with water
  3. customthe filtrate is evaporated under vacuum
  4. customThe residue obtained
  5. filtrationthe insoluble material is again filtered off
  6. customAfter evaporation of the filtrate, 13.2 g (78%) of 6-iodopyridine-3-carbaldehyde
  7. customare obtained in the form of a pale yellow solid with a melting point of 141° C.

Sources & evidence

ORD record
ord-0b9343cd3ba042419bf51874c35b0b14
Source dataset
uspto-grants-2011_06
Patent number
US07968560B2

Reaction notes

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