3-(benzyloxy)-1-methylpyridin-4(1H)-one → 4(1H)-Pyridinone, 3-hydroxy-1-methyl-

HRID 913010Notes

Reaction equation

HRID 913010 reaction equation
C([O:8][C:9]1[C:14](=[O:15])[CH:13]=[CH:12][N:11]([CH3:16])[CH:10]=1)C1C=CC=CC=1.[H][H]>CO.[Pd]>[OH:8][C:9]1[C:14](=[O:15])[CH:13]=[CH:12][N:11]([CH3:16])[CH:10]=1

Participants

5

Reactant 2

HCID 510516133-(benzyloxy)-1-methylpyridin-4(1H)-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 30849364(1H)-Pyridinone, 3-hydroxy-1-methyl-

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 3-benzyloxy-1-methyl-1H-pyridin-4-one (14.1 g, 65.5 mmol) and 10% Pd/C (1.20 g) in methanol was subjected to hydrogenation in a Parr apparatus under 50 psi pressure of hydrogen for 70 min. The mixture was filtered through a pad of CELITE™, the filtrate was concentrated to dryness, and the residue was triturated with acetone. The solid was then collected by suction filtration. The title compound was obtained as a light-brown powder (7.13 g, 87% yield) after vacuum oven drying. 1H NMR (400 MHz, DMSO-D6) δ (ppm): 7.49 (br. s, 1H), 7.38 (s, 1H), 6.12 (br. s, 1H) and 3.63 (s, 3H); MS-ESI (m/z): 125.7 [M+1]+.

Workup

  1. filtrationThe mixture was filtered through a pad of CELITE™
  2. concentrationthe filtrate was concentrated to dryness
  3. customthe residue was triturated with acetone
  4. filtrationThe solid was then collected by suction filtration

Sources & evidence

ORD record
ord-2e6e03a0af0443d9acd47fb26b222987
Source dataset
uspto-grants-2011_09
Patent number
US08026261B2

Reaction notes

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