1-(4-amino-3-fluoro-phenyl)-4-benzyloxy-1H-pyridin-2-one → 1-(4-Amino-3-fluoro-phenyl)-4-hydroxy-1H-pyridin-2-one

HRID 1784050Notes

Reaction equation

HRID 1784050 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:13]=[CH:12][C:11]([O:14]CC3C=CC=CC=3)=[CH:10][C:9]2=[O:22])=[CH:4][C:3]=1[F:23]>CO.[Pd]>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][C:9]2=[O:22])=[CH:4][C:3]=1[F:23]

Participants

4

Reactant 1

HCID 668824131-(4-amino-3-fluoro-phenyl)-4-benzyloxy-1H-pyridin-2-one

Product 1

HCID 668815431-(4-Amino-3-fluoro-phenyl)-4-hydroxy-1H-pyridin-2-oneYield 97%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 580 mg (1.87 mmol) 1-(4-amino-3-fluoro-phenyl)-4-benzyloxy-1H-pyridin-2-one (example 144, step 1) in 20 ml of MeOH was treated with 140 mg of Pd/C (10%) and hydrogenated at atmospheric pressure under vigorous stirring for 3 hrs. Filtration and evaporation of the solvent gave 398 mg (97%) of 1-(4-Amino-3-fluoro-phenyl)-4-hydroxy-1H-pyridin-2-one. Light brown solid. MS: 221 (M+H)+.

Workup

  1. filtrationFiltration and evaporation of the solvent

Sources & evidence

ORD record
ord-581c221020e9422f95f707d475439026
Source dataset
uspto-grants-2009_03
Patent number
US07501413B2

Reaction notes

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