Methyl (4-nitrophenoxy)acetate → Methyl(4-aminophenoxy)acetate

HRID 1419103Notes

Reaction equation

HRID 1419103 reaction equation
[N+:1]([C:4]1[CH:15]=[CH:14][C:7]([O:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])=[CH:6][CH:5]=1)([O-])=O.[H][H]>CO.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([O:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])=[CH:14][CH:15]=1

Participants

5

Reactant 2

HCID 700522Methyl (4-nitrophenoxy)acetateHCID 178418361HCID 178418361, compound

Product 1

HCID 6422115Methyl(4-aminophenoxy)acetateYield 97.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 30.8 g of methyl 4-nitrophenoxyacetate (prepared as described in Preparation 1) in 500 ml of methanol was shaken in an atmosphere of hydrogen and in the presence of 5.0 g of 10% w/w palladium-on-charcoal for 6 hours. At the end of this time, the reaction mixture was filtered and the filtrate was concentrated by evaporation under reduced pressure, to give 25.8 g of the title compound having an Rf value=0.79 (on thin layer chromatography on silica gel; developing solvent: ethyl acetate).

Workup

  1. filtrationAt the end of this time, the reaction mixture was filtered
  2. concentrationthe filtrate was concentrated by evaporation under reduced pressure

Sources & evidence

ORD record
ord-ca48524b311e48c6a9ac221dce326e50
Source dataset
uspto-grants-1999_03
Patent number
US05886014

Reaction notes

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