3-(1-cyano-1-methylethyl)-N-{4-methyl-3-[(6-nitropyridin-3-yl)oxy]phenyl}benzamide → N-{3-[(6-aminopyridin-3-yl)oxy]-4-methylphenyl}-3-(1-cyano-1-methylethyl)benzamide

HRID 1874603Notes

Reaction equation

HRID 1874603 reaction equation
[C:1]([C:3]([C:6]1[CH:7]=[C:8]([CH:29]=[CH:30][CH:31]=1)[C:9]([NH:11][C:12]1[CH:17]=[CH:16][C:15]([CH3:18])=[C:14]([O:19][C:20]2[CH:21]=[N:22][C:23]([N+:26]([O-])=O)=[CH:24][CH:25]=2)[CH:13]=1)=[O:10])([CH3:5])[CH3:4])#[N:2]>CO.[C].[Pd]>[NH2:26][C:23]1[N:22]=[CH:21][C:20]([O:19][C:14]2[CH:13]=[C:12]([NH:11][C:9](=[O:10])[C:8]3[CH:29]=[CH:30][CH:31]=[C:6]([C:3]([C:1]#[N:2])([CH3:5])[CH3:4])[CH:7]=3)[CH:17]=[CH:16][C:15]=2[CH3:18])=[CH:25][CH:24]=1

Participants

4

Reactant 1

HCID 687235843-(1-cyano-1-methylethyl)-N-{4-methyl-3-[(6-nitropyridin-3-yl)oxy]phenyl}benzamide

Product 1

HCID 68724247N-{3-[(6-aminopyridin-3-yl)oxy]-4-methylphenyl}-3-(1-cyano-1-methylethyl)benzamideYield 78.1%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

To a solution of 3-(1-cyano-1-methylethyl)-N-{4-methyl-3-[(6-nitropyridin-3-yl)oxy]phenyl}benzamide (6.68 g, 16.0 mmol) in methanol (150 mL) was added 10% palladium-carbon (850 mg), and the mixture was stirred at room temperature for 16 hr under a hydrogen atmosphere (2.0 atm). The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was recrystallized from ethyl acetate and hexane to give the title compound (4.83 g, 78%) as colorless crystals.

Workup

  1. filtrationThe insoluble material was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe obtained residue was recrystallized from ethyl acetate and hexane

Sources & evidence

ORD record
ord-28d07a5d9617400e800a46aaacad5eb4
Source dataset
uspto-grants-2012_11
Patent number
US08304557B2

Reaction notes

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