4-[3-(4-Methylphenyl)-1-propenyl]nitrobenzene → 4-[3-(4-Methylphenyl)propyl]aniline

HRID 1903654Notes

Reaction equation

HRID 1903654 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH:9]=[CH:10][C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-])=O)=[CH:13][CH:12]=2)=[CH:4][CH:3]=1>C(O)C.[C].[Pd]>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][CH2:10][C:11]2[CH:12]=[CH:13][C:14]([NH2:17])=[CH:15][CH:16]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 537641644-[3-(4-Methylphenyl)-1-propenyl]nitrobenzene

Product 1

HCID 133042544-[3-(4-Methylphenyl)propyl]anilineYield 91.1%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

To a solution of 4-[3-(4-methylphenyl)-1-propenyl]nitrobenzene (20 g) in ethanol (100 ml), 10% palladium-carbon (10 g) was added, and the resultant mixture was subjected to catalytic reduction under a pressure of 50 atm. After removal of the solvent from the reaction mixture by distillation, the residue was distilled under reduced pressure to give 4-[3-(4-methylphenyl)propyl]aniline (16.2 g). B.P. 135°-145° C./0.15 mmHg.

Workup

  1. customAfter removal of the solvent from the reaction mixture
  2. distillationby distillation
  3. distillationthe residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-3d99f0954f694051b92f1080b03e4c61
Source dataset
uspto-grants-1984_03
Patent number
US04437880

Reaction notes

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