Ethyl (3-nitrophenyl)acetate → Ethyl 2-(3-aminophenyl)acetate

HRID 1696429Notes

Reaction equation

HRID 1696429 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:7]=[CH:8][CH:9]=1)([O-])=O>CO.[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]([CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 1

HCID 14997011Ethyl (3-nitrophenyl)acetate

Product 1

HCID 13042040Ethyl 2-(3-aminophenyl)acetateYield 94.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of ethyl (3-nitrophenyl)acetate (21 g, 0.1 mol) and 10% Pd/C (2 g) in MeOH (300 mL) was stirred at RT under H2 40 (psi) for 2 h. The reaction mixture was filtered and the filtrate was concentrated to afford ethyl (3-aminophenyl)acetate (17 g). MS (ESI) m/z: 180 (M+H+).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-e649c546a045455fbf792655a090ceee
Source dataset
uspto-grants-2012_04
Patent number
US08163756B2

Reaction notes

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