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

HRID 1626887Notes

Reaction equation

HRID 1626887 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-058efb361754485ca05a5e89e2c29ebe
Source dataset
uspto-grants-2014_07
Patent number
US08785474B2

Reaction notes

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