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

HRID 390596Notes

Reaction equation

HRID 390596 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].[Mn+2]>[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-carbaldehydeYield 74%

Reagents, catalysts & solvents 2

HCID 160959Manganese oxideCatalystHCID 6344DichloromethaneSolvent

Procedure

86 g (987 mol) of manganese (II) oxide are added to a solution of 23.2 g (98.7 mmol) of (6-iodopyrid-3-yl)methanol in 800 mL of dichloromethane. The reaction mixture is stirred at room temperature for 22 hours. The reaction mixture is filtered through Celite and rinsed with dichloromethane. The filtrate is evaporated under vacuum to give 17 g (74%) of 6-iodopyridine-3-carbaldehyde in the form of a yellow solid.

Workup

  1. filtrationThe reaction mixture is filtered through Celite
  2. washrinsed with dichloromethane
  3. customThe filtrate is evaporated under vacuum

Sources & evidence

ORD record
ord-59f54983381a4a138629797dbf0435ea
Source dataset
uspto-grants-2013_02
Patent number
US08383652B2

Reaction notes

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