3-(2-Methoxyphenoxy)-2-nitro-5-(pyridin-3-yloxy)-aniline → 3-(2-Methoxyphenoxy)-5-(pyridin-3-yloxy)-benzene-1,2-diamine

HRID 13246Notes

Reaction equation

HRID 13246 reaction equation
[CH3:1][O:2][C:3]1[CH:26]=[CH:25][CH:24]=[CH:23][C:4]=1[O:5][C:6]1[C:7]([N+:20]([O-])=O)=[C:8]([CH:10]=[C:11]([O:13][C:14]2[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=2)[CH:12]=1)[NH2:9].[H][H]>[OH-].[Pd+2].[OH-].[C].CO>[CH3:1][O:2][C:3]1[CH:26]=[CH:25][CH:24]=[CH:23][C:4]=1[O:5][C:6]1[CH:12]=[C:11]([O:13][C:14]2[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=2)[CH:10]=[C:8]([NH2:9])[C:7]=1[NH2:20]

Participants

5

Reactant 2

HCID 231451253-(2-Methoxyphenoxy)-2-nitro-5-(pyridin-3-yloxy)-anilineHCID 178418361HCID 178418361, compound

Product 1

HCID 231457673-(2-Methoxyphenoxy)-5-(pyridin-3-yloxy)-benzene-1,2-diamine

Reagents, catalysts & solvents 2

HCID 178502593HCID 178502593, compoundCatalystHCID 887MethanolSolvent

Procedure

1 g of 20% palladium hydroxide-carbon catalyst was added to a methanol (20 ml) solution of 1.33 g of 3-(2-methoxyphenoxy)-2-nitro-5-(pyridin-3-yloxy)-aniline, and the reaction liquid was stirred for 4 hours in a hydrogen atmosphere. The catalyst was removed through filtration, the solvent was evaporated away under reduced pressure, and the resulting residue was purified through silica gel column chromatography (developing solvent: hexane/ethyl acetate=1/2 to ethyl acetate) to obtain the entitled compound as a pale orange oily substance.

Workup

  1. customthe reaction liquid
  2. customThe catalyst was removed through filtration
  3. customthe solvent was evaporated away under reduced pressure
  4. customthe resulting residue was purified through silica gel column chromatography (developing solvent: hexane/ethyl acetate=1/2 to ethyl acetate)
  5. customto obtain the entitled compound as a pale orange oily substance

Sources & evidence

ORD record
ord-4641b972407043e1a500a636dc54e740
Source dataset
uspto-grants-2010_06
Patent number
US07728025B2

Reaction notes

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