Hydrochloric Acid → 2-(4-Aminophenyl)propiononitrile

HRID 1956095Notes

Reaction equation

HRID 1956095 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:8](#[N:11])[CH:9]=[CH2:10].Cl.[Cl-].[Al+3].[Cl-].[Cl-]>ClCCl.CCCCCCC>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH:9]([CH3:10])[C:8]#[N:11])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric Acid2×HCID 6115AnilineHCID 7855AcrylonitrileHCID 6451240Aluminum(III) Chloride

Product 1

HCID 1200112-(4-Aminophenyl)propiononitrileYield 30.8%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8900HeptaneSolvent

Procedure

To 4.95 g aniline (53.128 mmol) are added 2.82 g acrylonitrile (53.128 mmol) and 3.89 ml heptane. A dry HCl gasflow is lead through the solution. Aluminiumchloride (4.10 g; 30.726 mmol) is added portionwise in 2.5 hours. The HCl flow is stopped and the reaction mixture is stored overnight at 0° C. After reflux for 1 hour, the reaction mixture is poured on ice, and dichloromethane is added. The organic phase is washed with 10% aqueous KCl-solution (4x) and, after drying, evaporated. The oil obtained is purified by column chromatography, yielding 2,39 g 4-aminophenylpropionitrile.

Workup

  1. temperatureAfter reflux for 1 hour
  2. additionis added
  3. washThe organic phase is washed with 10% aqueous KCl-solution (4x)
  4. customafter drying
  5. customevaporated
  6. customThe oil obtained
  7. customis purified by column chromatography

Sources & evidence

ORD record
ord-a8138e9663f644e9965c6c064e7011c7
Source dataset
uspto-grants-1998_07
Patent number
US05780008

Reaction notes

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