4-(4-Nitrophenyl)butyric acid → 4-(4-Aminophenyl)butanoic acid

HRID 1198191Notes

Reaction equation

HRID 1198191 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][CH2:12][C:13]([OH:15])=[O:14])=[CH:6][CH:5]=1)([O-])=O.[H][H]>[Pd].C(O)C>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([CH2:10][CH2:11][CH2:12][C:13]([OH:15])=[O:14])=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 797114-(4-Nitrophenyl)butyric acidHCID 178418361HCID 178418361, compound

Product 1

HCID 270494-(4-Aminophenyl)butanoic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 4-(4-nitrophenyl)butyric acid (3 g, 14 mmol) (Aldrich Chemical Company Ltd.) and 10% palladium on charcoal catalyst (0.3 g) in ethanol (100 ml) was submitted to gaseous hydrogen at 50 p.s.i., 20° C., for 30 minutes. The mixture was then filtered and concentrated. The resulting solid residue was recrystallised from isopropanol to give 4-(4-aminophenyl)butyric acid. (1.9 g, 76%) mp. 125°-127° C.

Workup

  1. filtrationThe mixture was then filtered
  2. concentrationconcentrated
  3. customThe resulting solid residue was recrystallised from isopropanol

Sources & evidence

ORD record
ord-b230434bc468430591a338c5420d4c00
Source dataset
uspto-grants-1994_01
Patent number
US05280043

Reaction notes

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