6-Chloro-4-hydroxy-5-phenylpyridin-2(1H)-one → 4-Hydroxy-5-phenylpyridin-2(1H)-one

HRID 1895729Notes

Reaction equation

HRID 1895729 reaction equation
Cl[C:2]1[NH:7][C:6](=[O:8])[CH:5]=[C:4]([OH:9])[C:3]=1[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>[Pd].CCO>[OH:9][C:4]1[C:3]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)=[CH:2][NH:7][C:6](=[O:8])[CH:5]=1

Participants

4

Reactant 1

HCID 546873076-Chloro-4-hydroxy-5-phenylpyridin-2(1H)-one

Product 1

HCID 546832584-Hydroxy-5-phenylpyridin-2(1H)-oneYield 58%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

A suspension of palladium on carbon (480 mg, 50 wt % wet, 0.451 mmol) and 6-chloro-4-hydroxy-5-phenylpyridin-2(1H)-one (1000 mg, 4.51 mmol) in EtOH (40 mL) was placed under a hydrogen balloon and stirred at 60° C. After stirring under hydrogen for 30 h, the mixture was filtered while hot through a pad of CELITE® 545 filter aid and rinsed with hot ethanol. The filtrate was concentrated to give 490 mg crude product as a yellow solid. MS (ESI) 188 (M+H).

Workup

  1. stirringAfter stirring under hydrogen for 30 h
  2. filtrationthe mixture was filtered while hot through a pad of CELITE® 545
  3. filtrationfilter aid
  4. washrinsed with hot ethanol
  5. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-7e7d5ab8dfc441edbf232d8163559e65
Source dataset
uspto-grants-2013_08
Patent number
US08513424B2

Reaction notes

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