5-(benzyloxy)-2-methylpyridin-4(1H)-one → 5-hydroxy-2-methylpyridin-4(1H)-one

HRID 1187470Notes

Reaction equation

HRID 1187470 reaction equation
C([O:8][C:9]1[C:10](=[O:16])[CH:11]=[C:12]([CH3:15])[NH:13][CH:14]=1)C1C=CC=CC=1>CO.O.[Pd]>[OH:8][C:9]1[C:10](=[O:16])[CH:11]=[C:12]([CH3:15])[NH:13][CH:14]=1

Participants

5

Reactant 1

HCID 63247195-(benzyloxy)-2-methylpyridin-4(1H)-one

Product 1

HCID 6426495-hydroxy-2-methylpyridin-4(1H)-oneYield 70.5%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of 5-benzyloxy-2-methyl-1H-pyridin-4-one (2 g, 9.29 mmol) in methanol (30 ml) and water (8 ml) was placed in a Parr bottle. 10% Pd/C was added and the mixture was hydrogenated at 50 psi for 3 hours. A bed of CELITE™ was placed on a sintered glass, and washed with 0.1N HCl and then water. The content in the Parr bottle was removed from the Parr hydrogenator and flushed with nitrogen. The solution was filtered under suction. The filtrate was evaporated to give a white solid (820 mg, 70% yield).

Workup

  1. washwashed with 0.1N HCl
  2. customThe content in the Parr bottle was removed from the Parr hydrogenator
  3. customflushed with nitrogen
  4. filtrationThe solution was filtered under suction
  5. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-2b44199cd4514f1d851c7ec6e91eaf55
Source dataset
uspto-grants-2014_03
Patent number
US08673943B2

Reaction notes

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