Ethyl 2-nitrophenylacetate → Ethyl 2-(2-aminophenyl)acetate

HRID 1458617Notes

Reaction equation

HRID 1458617 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])([O-])=O>C(O)C.[Pd]>[NH2:1][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12]

Participants

4

Reactant 1

HCID 595882Ethyl 2-nitrophenylacetate

Product 1

HCID 5743383Ethyl 2-(2-aminophenyl)acetate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of ethyl 2-nitrophenylacetate (13.6 g, 0.065 mole) in ethanol (150 ml) was hydrogenated over 10% Pd/C catalyst (1 g) at room temperature and pressure for 18 hours. The reaction mixture was filtered through keiselguhr and concentrated in vacuo to afford the title compound as a clear oil, which solidified on standing (10.8 g, 93%).

Workup

  1. filtrationThe reaction mixture was filtered through keiselguhr
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e247fe83154947c181ac5749405dca24
Source dataset
uspto-grants-1998_12
Patent number
US05852014

Reaction notes

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