Acrylonitrile → 3-(3-Chloroanilino)propanenitrile

HRID 426054Notes

Reaction equation

HRID 426054 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH2:8])[CH:5]=[CH:6][CH:7]=1.[C:9](#[N:12])[CH:10]=[CH2:11]>CC([O-])=O.CC([O-])=O.[Cu+2]>[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][CH2:11][CH2:10][C:9]#[N:12])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 7855Acrylonitrile2×HCID 79323-Chloroaniline

Product 1

HCID 2875943-(3-Chloroanilino)propanenitrileYield 67%

Reagents, catalysts & solvents 1

HCID 8895Cupric acetateCatalyst

Procedure

To a solution of 3-chlorobenzenamine (10 g, 0.079 mol) and acrylonitrile (5.0 g, 0.095 mol), Cu(OAc)2 (0.5 g, 5% by weight of 3-chlorobenzenamine), were heated under reflux, beginning at about 95° C. The reaction is heated at reflux for 3 h with the temperature rising to ˜130° C. Upon completion of the reaction, the acrylonitrile was stripped under reduced pressure. The residue was purified by column chromatography to afford the pure product 3-(3-chlorophenylamino)propanenitrile (8 g, yield 67%).

Workup

  1. temperatureunder reflux
  2. custombeginning at about 95° C
  3. temperatureThe reaction is heated
  4. temperatureat reflux for 3 h with the temperature
  5. customrising to ˜130° C
  6. customUpon completion of the reaction
  7. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-f0539804b37740a4b32ad2828586f14b
Source dataset
uspto-grants-2012_01
Patent number
US08106221B2

Reaction notes

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