2-(4-Nitrophenyl)butanol → 2-(4-Aminophenyl)butanol

HRID 1074445Notes

Reaction equation

HRID 1074445 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]([CH2:13][CH3:14])[CH2:11][OH:12])=[CH:6][CH:5]=1)([O-])=O>[Pd].C(O)C>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([CH:10]([CH2:13][CH3:14])[CH2:11][OH:12])=[CH:8][CH:9]=1

Participants

4

Reactant 1

HCID 204966922-(4-Nitrophenyl)butanol

Product 1

HCID 131457182-(4-Aminophenyl)butanol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution was prepared from 12.9 g of 2-(4-nitrophenyl)butanol and 250 ml of absolute ethanol, 0.65 g of 10% palladium on charcoal catalyst was added and the mixture was hydrogenated in a Parr apparatus at about 2.7 atmospheres for 2 hours. The catalyst was removed by filtration and the solvent was evaporated from the filtrate to leave a crude oil which was purified by kugelrohr distillation (115° C. at 0.2 mm pressure) to give 2-(4-aminophenyl)butanol as a clear-white liquid.

Workup

  1. additionwas added
  2. customThe catalyst was removed by filtration
  3. customthe solvent was evaporated from the filtrate
  4. customto leave a crude oil which
  5. distillationwas purified by kugelrohr distillation (115° C. at 0.2 mm pressure)

Sources & evidence

ORD record
ord-4c3ad1616912479a895b172bc1b306ca
Source dataset
uspto-grants-1983_07
Patent number
US04391818

Reaction notes

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