3-Nitrophenylacetic acid → (3-Aminophenyl)acetic acid

HRID 2351261Notes

Reaction equation

HRID 2351261 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH2:10][C:11]([OH:13])=[O:12])[CH:7]=[CH:8][CH:9]=1)([O-])=O>C(O)C.[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]([CH2:10][C:11]([OH:13])=[O:12])[CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 1

HCID 158763-Nitrophenylacetic acid

Product 1

HCID 571807(3-Aminophenyl)acetic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

3-Aminophenylacetic acid was prepared from a solution of 3-nitrophenylacetic acid (5.08 g, 28 mmol) in absolute ethanol (100 ml) which was hydrogenated at 40° C. and 40 psi in the presence of 5% Pd/C catalyst for 3 hours. The catalyst was removed by filtration, and upon removal of the solvent in vacuo, a highly viscous yellow oil remained which resisted crystallization.

Workup

  1. customwas hydrogenated at 40° C.
  2. customThe catalyst was removed by filtration
  3. customupon removal of the solvent in vacuo
  4. customcrystallization

Sources & evidence

ORD record
ord-28e4e25f90fc44b4ace4db345bd1b141
Source dataset
uspto-grants-1989_10
Patent number
US04873075

Reaction notes

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