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

HRID 1282018Notes

Reaction equation

HRID 1282018 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>O.CO.[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 acidYield 85%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

10 g (0.05 mol) of 2-(4-nitrophenyl)propanoic acid were dissolved in a mixture of 5 ml of water and 100 ml of methanol and 0.65 g of Pd/C 5% were added. The mixture was submitted to hydrogenation at 60 psi for 2 hours at room temperature. After the separation of the catalyst by filtration on celite the methanol was evaporated under vacuum and the title compound was crystallised from water on cooling (7 g; 85 % yield).

Workup

  1. additionwere added
  2. customAfter the separation of the catalyst
  3. filtrationby filtration on celite the methanol
  4. customwas evaporated under vacuum
  5. customthe title compound was crystallised from water
  6. temperatureon cooling (7 g; 85 % yield)

Sources & evidence

ORD record
ord-d998a8eda74e4c9d9e2b8477e9f2eedf
Source dataset
uspto-grants-2002_09
Patent number
US06455559B1

Reaction notes

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