Tetrahydrofuran → N-[3-(4-aminophenoxy)-4-methoxyphenyl]-3-(1-cyano-1-methylethyl)benzamide

HRID 2190411Notes

Reaction equation

HRID 2190411 reaction equation
[C:1]([C:3]([C:6]1[CH:7]=[C:8]([CH:30]=[CH:31][CH:32]=1)[C:9]([NH:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([O:20][C:21]2[CH:26]=[CH:25][C:24]([N+:27]([O-])=O)=[CH:23][CH:22]=2)[CH:13]=1)=[O:10])([CH3:5])[CH3:4])#[N:2].O1CCCC1>CO.[C].[Pd]>[NH2:27][C:24]1[CH:23]=[CH:22][C:21]([O:20][C:14]2[CH:13]=[C:12]([NH:11][C:9](=[O:10])[C:8]3[CH:30]=[CH:31][CH:32]=[C:6]([C:3]([C:1]#[N:2])([CH3:5])[CH3:4])[CH:7]=3)[CH:17]=[CH:16][C:15]=2[O:18][CH3:19])=[CH:26][CH:25]=1

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 673133033-(1-cyano-1-methylethyl)-N-[4-methoxy-3-(4-nitrophenoxy)phenyl]benzamide

Product 1

HCID 67312983N-[3-(4-aminophenoxy)-4-methoxyphenyl]-3-(1-cyano-1-methylethyl)benzamideYield 66%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

To a solution of 3-(1-cyano-1-methylethyl)-N-[4-methoxy-3-(4-nitrophenoxy)phenyl]benzamide (1.80 g, 4.17 mmol) in methanol (5 mL)/tetrahydrofuran (5 mL) was added 10%-palladium carbon (1 g), and the mixture was vigorously stirred under a hydrogen atmosphere at room temperature for 18 hr. The catalyst was filtered off through celite, and the filtrate was concentrated under reduced pressure to give the title compound (1.10 g, 66%) as a colorless amorphous substance.

Workup

  1. filtrationThe catalyst was filtered off through celite
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-18b2b30d4d804d71b17d7aff4864801c
Source dataset
uspto-grants-2012_12
Patent number
US08324395B2

Reaction notes

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