Ethanol → 5-acetyl-N-[3,5-bis(trifluoromethyl)phenyl]-2-hydroxybenzamide

HRID 2384351Notes

Reaction equation

HRID 2384351 reaction equation
C(O)C.[C:4]([C:7]1[CH:8]=[CH:9][C:10]([O:30]CC2C=CC=CC=2)=[C:11]([CH:29]=1)[C:12]([NH:14][C:15]1[CH:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:18]=[C:17]([C:25]([F:28])([F:27])[F:26])[CH:16]=1)=[O:13])(=[O:6])[CH3:5]>[C].[Pd].O1CCCC1>[C:4]([C:7]1[CH:8]=[CH:9][C:10]([OH:30])=[C:11]([CH:29]=1)[C:12]([NH:14][C:15]1[CH:16]=[C:17]([C:25]([F:26])([F:27])[F:28])[CH:18]=[C:19]([C:21]([F:22])([F:23])[F:24])[CH:20]=1)=[O:13])(=[O:6])[CH3:5]

Participants

5

Reactant 2

HCID 702EthanolHCID 178602005-Acetyl-2-benzyloxy-N-[3,5-bis(trifluoromethyl)phenyl]benzamide

Product 1

HCID 103857615-acetyl-N-[3,5-bis(trifluoromethyl)phenyl]-2-hydroxybenzamideYield 47%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Ethanol (6 mL) and tetrahydrofuran (72 mL) were added to 5-acetyl-2-benzyloxy-N-[3,5-bis(trifluoromethyl)phenyl]benzamide (602 mg, 1.25 mmol) and 5% palladium-carbon (60 mg), and the mixture was hydrogenated at room temperature for 30 minutes. After the insoluble matter was filtered off, the solvent was evaporated under reduced pressure and the residue was recrystallized from n-hexane-ethyl acetate to give the title compound (230 mg, 47.0%) as a white solid.

Workup

  1. filtrationAfter the insoluble matter was filtered off
  2. customthe solvent was evaporated under reduced pressure
  3. customthe residue was recrystallized from n-hexane-ethyl acetate

Sources & evidence

ORD record
ord-b575c26132cf4307814682004085f9b9
Source dataset
uspto-grants-2012_09
Patent number
US08263657B2

Reaction notes

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