N-(4-nitrophenyl)pentanamide → N-(4-aminophenyl)pentanamide

HRID 461019Notes

Reaction equation

HRID 461019 reaction equation
[N+:1]([C:4]1[CH:16]=[CH:15][C:7]([NH:8][C:9](=[O:14])[CH2:10][CH2:11][CH2:12][CH3:13])=[CH:6][CH:5]=1)([O-])=O>C(O)C.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([NH:8][C:9](=[O:14])[CH2:10][CH2:11][CH2:12][CH3:13])=[CH:15][CH:16]=1

Participants

4

Reactant 1

HCID 3762929N-(4-nitrophenyl)pentanamide

Product 1

HCID 1725711N-(4-aminophenyl)pentanamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 4'-nitrovaleranilide (13.33 g., 0.06 mole) in absolute ethanol (750 ml.) is hydrogenated over 10% palladium on charcoal (2 g.) until the theoretical absorption is achieved. The catalyst is removed and the solvent is removed in vacuo. The residue is recrystallized from butyl chloride to yield 9.0 g., m.p. 81°-83° C.

Workup

  1. customThe catalyst is removed
  2. customthe solvent is removed in vacuo
  3. customThe residue is recrystallized from butyl chloride
  4. customto yield 9.0 g

Sources & evidence

ORD record
ord-1657976fc8b14bb1ae6485729ff31a32
Source dataset
uspto-grants-1977_12
Patent number
US04061763

Reaction notes

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