Water → 3-(4-Aminophenyl)propionic acid

HRID 725834Notes

Reaction equation

HRID 725834 reaction equation
[N+:1]([C:4]1[CH:14]=[CH:13][C:7]([CH:8]=[CH:9][C:10]([OH:12])=[O:11])=[CH:6][CH:5]=1)([O-])=O.O.[H][H]>CO.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([CH2:8][CH2:9][C:10]([OH:12])=[O:11])=[CH:13][CH:14]=1

Participants

6

Reactant 3

HCID 962WaterHCID 701562-Propenoic acid, 3-(4-nitrophenyl)-HCID 178418361HCID 178418361, compound

Product 1

HCID 754513-(4-Aminophenyl)propionic acidYield 99.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 155 g of 4-nitro-cinnamic acid in 1 l of methanol is mixed with 15 g of palladium on charcoal (10%) and 30 ml of water and hydrogenated at ambient temperature under 3 bar until no more hydrogen is taken up (2 hours). After filtration and evaporation of the solvent in a rotary evaporator, 2 lots of 300 ml of toluene are added in order to eliminate residual water and the solvent is distilled off in a rotary evaporator. In this way 132 g (quant.) of 3-(4-aminophenyl)propionic acid are obtained.

Workup

  1. custom(2 hours)
  2. filtrationAfter filtration and evaporation of the solvent
  3. customin a rotary evaporator, 2 lots of 300 ml of toluene
  4. additionare added in order
  5. distillationthe solvent is distilled off in a rotary evaporator

Sources & evidence

ORD record
ord-3854460a54784b7c98b1d7785b6ea196
Source dataset
uspto-grants-1998_01
Patent number
US05707989

Reaction notes

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