Hydrochloric Acid → 3-(4-aminophenoxy)-N-[4-(trifluoromethyl)phenyl]benzamide

HRID 2190420Notes

Reaction equation

HRID 2190420 reaction equation
[N+:1]([C:4]1[CH:29]=[CH:28][C:7]([O:8][C:9]2[CH:10]=[C:11]([CH:25]=[CH:26][CH:27]=2)[C:12]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][CH:16]=2)=[O:13])=[CH:6][CH:5]=1)([O-])=O.O1CCCC1.Cl>CO.[C].[Pd]>[NH2:1][C:4]1[CH:29]=[CH:28][C:7]([O:8][C:9]2[CH:10]=[C:11]([CH:25]=[CH:26][CH:27]=2)[C:12]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]([F:22])([F:23])[F:24])=[CH:17][CH:16]=2)=[O:13])=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 673114413-(4-nitrophenoxy)-N-[4-(trifluoromethyl)phenyl]benzamide

Product 1

HCID 673119133-(4-aminophenoxy)-N-[4-(trifluoromethyl)phenyl]benzamideYield 86%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

To a solution of 3-(4-nitrophenoxy)-N-[4-(trifluoromethyl)phenyl]benzamide (6.75 g, 16.8 mmol) in methanol (20 mL)/tetrahydrofuran (10 mL) were added 10%-palladium carbon (2 g) and concentrated hydrochloric acid (1 mL), and the mixture was vigorously stirred under a hydrogen atmosphere at room temperature for 3 hr. The catalyst was filtered off through celite, the filtrate was concentrated under reduced pressure, and the obtained residue was triturated with diethyl ether to give the title compound (5.37 g, 86%) as a white solid.

Workup

  1. filtrationThe catalyst was filtered off through celite
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customthe obtained residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-9529512fc8e541ab846eb18a9c16e42a
Source dataset
uspto-grants-2012_12
Patent number
US08324395B2

Reaction notes

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