3-(1-cyano-1-methylethyl)-N-[3-(4-nitrophenoxy)phenyl]benzamide → N-[3-(4-aminophenoxy)phenyl]-3-(1-cyano-1-methylethyl)benzamide

HRID 2190393Notes

Reaction equation

HRID 2190393 reaction equation
[C:1]([C:3]([C:6]1[CH:7]=[C:8]([CH:28]=[CH:29][CH:30]=1)[C:9]([NH:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([O:18][C:19]2[CH:24]=[CH:23][C:22]([N+:25]([O-])=O)=[CH:21][CH:20]=2)[CH:13]=1)=[O:10])([CH3:5])[CH3:4])#[N:2]>O1CCCC1.CO.[C].[Pd]>[NH2:25][C:22]1[CH:23]=[CH:24][C:19]([O:18][C:14]2[CH:13]=[C:12]([NH:11][C:9](=[O:10])[C:8]3[CH:28]=[CH:29][CH:30]=[C:6]([C:3]([C:1]#[N:2])([CH3:5])[CH3:4])[CH:7]=3)[CH:17]=[CH:16][CH:15]=2)=[CH:20][CH:21]=1

Participants

5

Reactant 1

HCID 573868263-(1-cyano-1-methylethyl)-N-[3-(4-nitrophenoxy)phenyl]benzamide

Product 1

HCID 57386827N-[3-(4-aminophenoxy)phenyl]-3-(1-cyano-1-methylethyl)benzamideYield 98%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(1-cyano-1-methylethyl)-N-[3-(4-nitrophenoxy)phenyl]benzamide (8.10 g, 20.2 mmol) in tetrahydrofuran (50 mL) and methanol (50 mL) was added 10% palladium-carbon (555 mg), and the mixture was stirred under a hydrogen atmosphere (2.5 atm) at room temperature for 14 hr. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure to give the title compound (7.34 g, 98%) as a pale-gray amorphous substance. The obtained compound was used in the next reaction without a further purification.

Workup

  1. filtrationThe insoluble material was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-2e08fdc4a94f463d8bcdccd551979ead
Source dataset
uspto-grants-2012_12
Patent number
US08324395B2

Reaction notes

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