Hydrogen Peroxide → N-(3,5-bis-trifluoromethyl-phenyl)-4-hydroxy-isophthalamide

HRID 1777407Notes

Reaction equation

HRID 1777407 reaction equation
[F:1][C:2]([F:26])([F:25])[C:3]1[CH:4]=[C:5]([NH:13][C:14](=[O:24])[C:15]2[CH:20]=[C:19]([C:21]#[N:22])C=[CH:17][C:16]=2O)[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[OH-:27].[Na+].OO.[CH3:31][OH:32].C(Cl)(Cl)Cl>C(O)C.CS(C)=O>[F:1][C:2]([F:25])([F:26])[C:3]1[CH:4]=[C:5]([NH:13][C:14](=[O:24])[C:15]2[CH:16]=[CH:17][C:31]([OH:32])=[C:19]([C:21]([NH2:22])=[O:27])[CH:20]=2)[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 9976653N-[3,5-Bis(trifluoromethyl)phenyl]-5-cyano-2-hydroxybenzamideHCID 21584188Chloroform methanol

Product 1

HCID 90313251N-(3,5-bis-trifluoromethyl-phenyl)-4-hydroxy-isophthalamideYield 95%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 702EthanolSolvent

Procedure

N-(3,5-bis-trifluoromethyl-phenyl)-5-cyano-2-hydroxy-benzamide (150 mg, 0.4 mmol) obtained in step 1 was dissolved in ethanol (1.74 ml) and DMSO (0.8 ml). 1 M NaOH (0.33 ml) was added thereto, to which 30% H2O2 (0.33 ml) was added. The reaction mixture was stirred overnight at room temperature. The solution was eliminated under reduced pressure. The residue proceeded to column chromatography (5% MeOH—CHCl3) to give 149 mg of the target compound (yield: 95%).

Sources & evidence

ORD record
ord-389b115b9eed474382e30b2d39ba0e00
Source dataset
uspto-grants-2016_02
Patent number
US09266872B2

Reaction notes

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