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

HRID 46497Notes

Reaction equation

HRID 46497 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-3396c84eaf1e4e19806d6ff0038281c7
Source dataset
uspto-grants-1979_11
Patent number
US04173646

Reaction notes

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