3-Nitrophenoxyacetic acid methyl ester → Methyl 2-(3-aminophenoxy)acetate

HRID 2189019Notes

Reaction equation

HRID 2189019 reaction equation
[CH3:1][O:2][C:3](=[O:15])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([N+:12]([O-])=O)[CH:7]=1>[Pd].CO>[CH3:1][O:2][C:3](=[O:15])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([NH2:12])[CH:7]=1

Participants

4

Reactant 1

HCID 107037043-Nitrophenoxyacetic acid methyl ester

Product 1

HCID 10678961Methyl 2-(3-aminophenoxy)acetate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Add 1.3 g of palladium on activated carbon (10%) to 13 g (61.6 mmol) of 3-nitrophenoxyacetic acid methyl ester in 150 ml of methanol under argon. Stir the mixture at RT under a hydrogen atmosphere (standard pressure) for 18 h. Filter the catalyst off through kieselguhr and concentrate the filtrate under reduced pressure. After drying under high vacuum, 10.7 g (95.9% of theory) of the target compound are obtained.

Workup

  1. filtrationFilter the catalyst off through kieselguhr
  2. concentrationconcentrate the filtrate under reduced pressure
  3. customAfter drying under high vacuum, 10.7 g (95.9% of theory) of the target compound
  4. customare obtained

Sources & evidence

ORD record
ord-d56ddf54de38434db21b0d6402665555
Source dataset
uspto-grants-2012_12
Patent number
US08324222B2

Reaction notes

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