Ethanol → N3-[3,5-bis(trifluoromethyl)phenyl]-4-hydroxy-N1,N1-dimethylisophthalamide

HRID 644423Notes

Reaction equation

HRID 644423 reaction equation
C([O:8][C:9]1[CH:19]=[CH:18][C:12]([C:13]([N:15]([CH3:17])[CH3:16])=[O:14])=[CH:11][C:10]=1[C:20]([NH:22][C:23]1[CH:28]=[C:27]([C:29]([F:32])([F:31])[F:30])[CH:26]=[C:25]([C:33]([F:36])([F:35])[F:34])[CH:24]=1)=[O:21])C1C=CC=CC=1.C(O)C>[Pd].C(OCC)(=O)C>[F:30][C:29]([F:31])([F:32])[C:27]1[CH:28]=[C:23]([NH:22][C:20](=[O:21])[C:10]2[CH:11]=[C:12]([CH:18]=[CH:19][C:9]=2[OH:8])[C:13]([N:15]([CH3:17])[CH3:16])=[O:14])[CH:24]=[C:25]([C:33]([F:35])([F:34])[F:36])[CH:26]=1

Participants

5

Reactant 2

HCID 702EthanolHCID 865955374-Benzyloxy-N3-[3,5-bis(trifluoromethyl)phenyl]-N1,N1-dimethylisophthalamide

Product 1

HCID 11750506N3-[3,5-bis(trifluoromethyl)phenyl]-4-hydroxy-N1,N1-dimethylisophthalamideYield 91.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4-benzyloxy-N3-[3,5-bis(trifluoromethyl)phenyl]-N1,N1-dimethyl-isophthalamide (141 mg, 0.28 mmol) and 5% Pd—C (14 mg) in a mixed solvent of ethanol (5 ml) and ethyl acetate (5 ml) was stirred at room temperature for 1 hour under hydrogen atmosphere. The reaction mixture was filtered and the filtrate was evaporated under reduced pressure to give the title compound (106 mg, 91.2%) as a white solid.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-b80f2f65e2dd407c98167430ed521d56
Source dataset
uspto-grants-2010_04
Patent number
US07700655B2

Reaction notes

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