Ethanol → 6-[5-hydroxy-2-(2,2,2-trifluoroethoxy)benzamidomethyl]-2(1H)-pyridone

HRID 542265Notes

Reaction equation

HRID 542265 reaction equation
C([O:8][C:9]1[CH:10]=[CH:11][C:12]([O:26][CH2:27][C:28]([F:31])([F:30])[F:29])=[C:13]([CH:25]=1)[C:14]([NH:16][CH2:17][C:18]1[NH:23][C:22](=[O:24])[CH:21]=[CH:20][CH:19]=1)=[O:15])C1C=CC=CC=1.C(O)C>[Pd].CO>[OH:8][C:9]1[CH:10]=[CH:11][C:12]([O:26][CH2:27][C:28]([F:31])([F:29])[F:30])=[C:13]([CH:25]=1)[C:14]([NH:16][CH2:17][C:18]1[NH:23][C:22](=[O:24])[CH:21]=[CH:20][CH:19]=1)=[O:15]

Participants

5

Reactant 2

HCID 702EthanolHCID 135635916-[5-benzyloxy-2-(2,2,2-trifluoroethoxy)benzamidomethyl]-2(1H)-pyridone

Product 1

HCID 135635926-[5-hydroxy-2-(2,2,2-trifluoroethoxy)benzamidomethyl]-2(1H)-pyridone

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 0.5 g of 6-[5-benzyloxy-2-(2,2,2-trifluoroethoxy)benzamidomethyl]-2(1H)-pyridone, 60 ml of ethanol, 40 ml of methanol and 0.043 g of 10% palladium on charcoal was hydrogenated on a Parr apparatus at about 20° C. for about 16 hours. Filtration followed by evaporation of the filtrate provided a residue which was triturated with acetonitrile. The solid was separated by filtration and washed with acetonitrile to provide 6-[5-hydroxy-2-(2,2,2-trifluoroethoxy)benzamidomethyl]-2(1H)-pyridone. The structural assignment was supported by infrared and nuclear magnetic resonance spectral analyses.

Workup

  1. filtrationFiltration
  2. customfollowed by evaporation of the filtrate
  3. customprovided a residue which
  4. customwas triturated with acetonitrile
  5. customThe solid was separated by filtration
  6. washwashed with acetonitrile

Sources & evidence

ORD record
ord-93bad705cda246638fd8592aa9b15d8b
Source dataset
uspto-grants-1987_04
Patent number
US04656285

Reaction notes

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