5-(2-Cyano-phenoxy)-4-(6-methanesulfonyl-pyridin-3-yloxy)-2-nitro-phenylamine → 4-(2-Cyano-phenoxy)-5-(6-methanesulfonyl-pyridin-3-yloxy)-benzene-1,2-diamine

HRID 13293Notes

Reaction equation

HRID 13293 reaction equation
[C:1]([C:3]1[CH:30]=[CH:29][CH:28]=[CH:27][C:4]=1[O:5][C:6]1[C:7]([O:16][C:17]2[CH:18]=[N:19][C:20]([S:23]([CH3:26])(=[O:25])=[O:24])=[CH:21][CH:22]=2)=[CH:8][C:9]([N+:13]([O-])=O)=[C:10]([NH2:12])[CH:11]=1)#[N:2].[H][H]>[Ni].CO>[C:1]([C:3]1[CH:30]=[CH:29][CH:28]=[CH:27][C:4]=1[O:5][C:6]1[CH:11]=[C:10]([NH2:12])[C:9]([NH2:13])=[CH:8][C:7]=1[O:16][C:17]1[CH:18]=[N:19][C:20]([S:23]([CH3:26])(=[O:24])=[O:25])=[CH:21][CH:22]=1)#[N:2]

Participants

5

Reactant 2

HCID 231457765-(2-Cyano-phenoxy)-4-(6-methanesulfonyl-pyridin-3-yloxy)-2-nitro-phenylamineHCID 178418361HCID 178418361, compound

Product 1

HCID 231453124-(2-Cyano-phenoxy)-5-(6-methanesulfonyl-pyridin-3-yloxy)-benzene-1,2-diamine

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

20 mg of developed Raney nickel catalyst was added to a methanol (5 ml) solution of 161 mg of 5-(2-cyano-phenoxy)-4-(6-methanesulfonyl-pyridin-3-yloxy)-2-nitro-phenylamine obtained in (step 4), and the reaction liquid was stirred overnight in a hydrogen atmosphere. The catalyst was removed through filtration, and the solvent was evaporated away under reduced pressure to obtain the entitled compound.

Workup

  1. customobtained in (step 4)
  2. customthe reaction liquid
  3. customThe catalyst was removed through filtration
  4. customthe solvent was evaporated away under reduced pressure
  5. customto obtain the entitled compound

Sources & evidence

ORD record
ord-c551551790b94dad95254f4cb76d0749
Source dataset
uspto-grants-2010_06
Patent number
US07728025B2

Reaction notes

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