HCID 54569294, compound → 3-Hexylaniline

HRID 2232414Notes

Reaction equation

HRID 2232414 reaction equation
[CH:1]([C:7]1[CH:8]=[C:9]([N+:13]([O-])=O)[CH:10]=[CH:11][CH:12]=1)=[CH:2][CH2:3][CH2:4][CH2:5][CH3:6].[H][H]>C(O)C.[Pd]>[CH2:1]([C:7]1[CH:8]=[C:9]([CH:10]=[CH:11][CH:12]=1)[NH2:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

5

Reactant 2

HCID 54569294HCID 54569294, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 5722403-HexylanilineYield 90.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

The 3-(1-hexenyl)nitrobenzene (11.0 g, 0.054 m) was dissolved in absolute ethanol (500 ml), treated with 1.1 g of 10% palladium on charcoal catalyst and hydrogenated on a Parr apparatus at about 45 psi for 21/2 hours. Hydrogen uptake had ceased. The reaction mixture was filtered to remove catalyst, concentrated under vacuum, and then resulting oil purified by Kuglrohr distillation (BP 75°-85° C. at 0.05 mm Hg) to yield 3-hexylaniline (8.6 g, 90% yield) as a clear colorless oil.

Workup

  1. custom2 hours
  2. filtrationThe reaction mixture was filtered
  3. customto remove catalyst
  4. concentrationconcentrated under vacuum
  5. customresulting oil
  6. distillationpurified by Kuglrohr distillation (BP 75°-85° C. at 0.05 mm Hg)

Sources & evidence

ORD record
ord-12db25c0d34f4f5da099e60db4a9b429
Source dataset
uspto-grants-1988_11
Patent number
US04788209

Reaction notes

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