4,5-Bis(benzyloxy)picolinaldehyde → 5-Hydroxy-4-oxo-1,4-dihydropyridine-2-carbaldehyde

HRID 1252619Notes

Reaction equation

HRID 1252619 reaction equation
C1(C[O:8][C:9]2[C:14]([O:15]CC3C=CC=CC=3)=[CH:13][N:12]=[C:11]([CH:23]=[O:24])[CH:10]=2)C=CC=CC=1.[H][H]>CN(C)C=O.[Pd]>[OH:15][C:14]1[C:9](=[O:8])[CH:10]=[C:11]([CH:23]=[O:24])[NH:12][CH:13]=1

Participants

5

Reactant 2

HCID 141825014,5-Bis(benzyloxy)picolinaldehydeHCID 178418361HCID 178418361, compound

Product 1

HCID 141825025-Hydroxy-4-oxo-1,4-dihydropyridine-2-carbaldehydeYield 76.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of 4,5-bis(phenylmethoxy)-2-pyridinecarboxaldehyde (1.9 g, 6.0 mmol) in 25 ml of dry dimethylformamide was added 0.2 g of palladium on charcoal catalyst and hydrogen was bubbled through the mixture for three hours. The catalyst was removed by filtration, the solvent distilled off in vacuo and the residue triturated with ether to give 0.64 g of the title compound, melting point 174°-177° C., dec.

Workup

  1. customwas bubbled through the mixture for three hours
  2. customThe catalyst was removed by filtration
  3. distillationthe solvent distilled off in vacuo
  4. customthe residue triturated with ether

Sources & evidence

ORD record
ord-9df813cbee8543d98e8158497967b429
Source dataset
uspto-grants-1988_05
Patent number
US04743685

Reaction notes

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