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

HRID 1626897Notes

Reaction equation

HRID 1626897 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

A mixture of 1 (6.7 g, 1 mmol) in THF (100 ml) and EtOH (100 ml) is slowly added 10% Pd/C (680 mg) at room temperature. The reaction mixture is hydrogenated for 24 h with H2 balloon at room temperature. The mixture is filtered through celite pad and washed with EtOH. The filtrate is concentrated in vacuo.

Workup

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

Sources & evidence

ORD record
ord-86e407f29b444f868fa8ea271ca68a79
Source dataset
uspto-grants-2014_07
Patent number
US08785474B2

Reaction notes

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