HCID 23153294, compound → HCID 23153189, compound

HRID 492707Notes

Reaction equation

HRID 492707 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][C:15]=1[N+:16]([O-])=O)[O:5][C:6]1[CH:11]=[CH:10][N:9]=[C:8]([NH2:12])[CH:7]=1>CO.[C].[Pd]>[NH2:16][C:15]1[CH:14]=[CH:13][C:4]([O:5][C:6]2[CH:11]=[CH:10][N:9]=[C:8]([NH2:12])[CH:7]=2)=[CH:3][C:2]=1[CH3:1]

Participants

4

Reactant 1

HCID 23153294HCID 23153294, compound

Product 1

HCID 23153189HCID 23153189, compoundYield 53.1%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

To a solution of 4-(3-methyl-4-nitrophenoxy)pyridin-2-ylamine (1.64 g, 6.69 mmol) in methanol (75 ml) was added 10% palladium carbon (300 mg), followed by stirring under a hydrogen atmosphere at room temperature 14.5 hrs. The reaction mixture was filtered to remove the catalyst. The filtrate was concentrated under a reduced pressure to give a residue, which was purified by silica gel column chromatography (eluent; hexane:ethyl acetate=1:2, ethyl acetate, then ethyl acetate:methanol=20:1 to 10:1) to provide the titled compound (765 mg, 53.1%) as a brown solid.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customto remove the catalyst
  3. concentrationThe filtrate was concentrated under a reduced pressure
  4. customto give a residue, which
  5. customwas purified by silica gel column chromatography (eluent

Sources & evidence

ORD record
ord-518e89130dca4157be68d0e8681c9ba4
Source dataset
uspto-grants-2009_05
Patent number
US07531532B2

Reaction notes

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