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

HRID 644408Notes

Reaction equation

HRID 644408 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]>[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 23938PalladiumCatalystHCID 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 on 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-ef6d9b3e13ed499e9e853bc03ae79e08
Source dataset
uspto-grants-2010_04
Patent number
US07700655B2

Reaction notes

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