m-Nitrophenethyl acetate → 2-(3-Aminophenyl)ethyl acetate

HRID 1247641Notes

Reaction equation

HRID 1247641 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH2:10][CH2:11][O:12][C:13](=[O:15])[CH3:14])[CH:7]=[CH:8][CH:9]=1)([O-])=O>C(OCC)(=O)C.[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]([CH2:10][CH2:11][O:12][C:13](=[O:15])[CH3:14])[CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 1

HCID 110451m-Nitrophenethyl acetate

Product 1

HCID 587222382-(3-Aminophenyl)ethyl acetate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of acetic acid 2-(3-nitro-phenyl)-ethyl ester (15 g, 71.7 mmol) (from Example 3a supra) in ethyl acetate (150 mL), was added 10% palladium on carbon (1.5 g) (Aldrich). This mixture was hydrogenated at room temperature on the Parr apparatus at 50 psi for one hour. The reaction mixture was filtered over a bed of Celite® and washed with ethyl acetate. The filtrate was concentrated under reduced pressure to give acetic acid 2-(3-amino-phenyl)-ethyl ester. (Yield 12.81 g, 71.48 mmol, 99%).

Workup

  1. filtrationThe reaction mixture was filtered over a bed of Celite®
  2. washwashed with ethyl acetate
  3. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-cc969d9796c8474bba66811f7453b62b
Source dataset
uspto-grants-2006_10
Patent number
US07129351B2

Reaction notes

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