2-(3-Cyanophenylamino)-6-chloro-3-nitropyridine → 3-(3-Amino-6-chloropyridin-2-ylamino)benzonitrile

HRID 1890666Notes

Reaction equation

HRID 1890666 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=2)[C:12]#[N:13])[C:5]([N+:17]([O-])=O)=[CH:4][CH:3]=1>[Ni].CO.ClCCl>[NH2:17][C:5]1[C:6]([NH:8][C:9]2[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=2)[C:12]#[N:13])=[N:7][C:2]([Cl:1])=[CH:3][CH:4]=1

Participants

4

Reactant 1

HCID 433302912-(3-Cyanophenylamino)-6-chloro-3-nitropyridine

Product 1

HCID 583356623-(3-Amino-6-chloropyridin-2-ylamino)benzonitrile

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 21226129Dichloromethane methanolSolvent

Procedure

In step 1-2, Raney nickel was added to a suspension of 3-(6-chloro-3-nitropyridin-2-ylamino)benzonitrile in methanol/dichloromethane (1:1) and the resulting suspension was set up in Parr shaker under a hydrogen atmosphere (40 psi) for 18 hours. The remaining catalyst was removed through a Celite pad, and the reaction mixture was concentrated to afford the crude product 3-(3-amino-6-chloropyridin-2-ylamino)benzonitrile (1-2) which was used in the next step without further purification.

Workup

  1. customfor 18 hours
  2. customThe remaining catalyst was removed through a Celite pad
  3. concentrationthe reaction mixture was concentrated

Sources & evidence

ORD record
ord-095e280023ea448c9093750d3dfc618f
Source dataset
uspto-grants-2013_08
Patent number
US08507488B2

Reaction notes

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