2-(4-Nitrophenyl)propionic acid → 4-Aminohydratropic acid

HRID 660330

Reaction equation

HRID 660330 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]([CH3:14])[C:11]([OH:13])=[O:12])=[CH:6][CH:5]=1)([O-])=O>C1COCC1.CCO.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([CH:10]([CH3:14])[C:11]([OH:13])=[O:12])=[CH:8][CH:9]=1

Participants

5

Reactant 1

HCID 892442-(4-Nitrophenyl)propionic acid

Product 1

HCID 430264-Aminohydratropic acid

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 2-(4-nitrophenyl)propionic acid (2.05 g) in THF (20 mL) and EtOH (20 mL) was slowly added 10% Pd/C (0.21 g) at room temperature. After hydrogenated for 2 h with H2 balloon, the reaction mixture was filtered through celite pad and washed with EtOH. The filtrate was concentrated in vacuo to afford the product as pale brown solid. (1.75 g, quantitative)

Workup

  1. customat room temperature
  2. filtrationthe reaction mixture was filtered through celite pad
  3. washwashed with EtOH
  4. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-ae78d0401a8b4ca7a923ce6f9ad8b273
Source dataset
uspto-grants-2011_12
Patent number
US08084484B2

Linked notes

Loading…