Water → 6-Iodo-5-methoxypicolinaldehyde

HRID 55277Notes

Reaction equation

HRID 55277 reaction equation
[OH:1][CH2:2][C:3]1[N:8]=[C:7]([I:9])[C:6]([O:10][CH3:11])=[CH:5][CH:4]=1.O>C1(C)C=CC=CC=1.[O-2].[O-2].[Mn+4]>[I:9][C:7]1[C:6]([O:10][CH3:11])=[CH:5][CH:4]=[C:3]([CH:2]=[O:1])[N:8]=1

Participants

5

Reactant 2

HCID 962WaterHCID 19957482(6-Iodo-5-methoxypyridin-2-yl)methanol

Product 1

HCID 199574546-Iodo-5-methoxypicolinaldehydeYield 44.8%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 1140TolueneSolvent

Procedure

175 g of manganese dioxide is added to a solution of 29 g of 6-hydroxymethyl-2-iodo-3-methoxypyridine in 600 ml of toluene, and the suspension is heated with stirring and refluxed for three hours on a water separator. The reaction mixture is filtered, the filter residue is washed with dichloromethane, the filtrate is dried on sodium sulfate and concentrated by evaporation. The crude product is chromatographed on silica gel with hexane/0-25% ethyl acetate. 12.9 g of 2-iodo-3-methoxypyridine-6-aldehyde of melting point 118°-121° C. is obtained.

Workup

  1. temperaturethe suspension is heated
  2. filtrationThe reaction mixture is filtered
  3. washthe filter residue is washed with dichloromethane
  4. customthe filtrate is dried on sodium sulfate
  5. concentrationconcentrated by evaporation
  6. customThe crude product is chromatographed on silica gel with hexane/0-25% ethyl acetate

Sources & evidence

ORD record
ord-c265293070cd4be9bfbdf251406d53eb
Source dataset
uspto-grants-1997_04
Patent number
US05624943

Reaction notes

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