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

HRID 1874594Notes

Reaction equation

HRID 1874594 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:20]=[N:21][C:22]([N+:25]([O-])=O)=[CH:23][CH:24]=2)[CH:13]=1)=[O:10])([CH3:5])[CH3:4])#[N:2]>CO.[C].[Pd]>[NH2:25][C:22]1[N:21]=[CH:20][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])([CH3:4])[CH3:5])[CH:7]=3)[CH:17]=[CH:16][CH:15]=2)=[CH:24][CH:23]=1

Participants

4

Reactant 1

HCID 687232483-(1-cyano-1-methylethyl)-N-{3-[(6-nitropyridin-3-yl)oxy]phenyl}benzamide

Product 1

HCID 57386822N-{3-[(6-aminopyridin-3-yl)oxy]phenyl}-3-(1-cyano-1-methylethyl)benzamideYield 79.7%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

To a solution of 3-(1-cyano-1-methylethyl)-N-{3-[(6-nitropyridin-3-yl)oxy]phenyl}benzamide (6.00 g, 14.9 mmol) in methanol (150 mL) was added 10% palladium-carbon (790 mg), and the mixture was stirred at room temperature for 20 hr under a hydrogen atmosphere (3.0 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 (4.42 g, 79%) 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-09c279226a29418fa4bf202efa7ffcf4
Source dataset
uspto-grants-2012_11
Patent number
US08304557B2

Reaction notes

Loading…