Acrylonitrile → 3-(3-Chloroanilino)propanenitrile

HRID 426049Notes

Reaction equation

HRID 426049 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

A solution of 3-chlorobenzenamine (10 g, 0.079 mol), Cu(OAc)2 (0.5 g, 5% by weight of m-chloroaniline), and acrylonitrile, was heated to reflux. Refluxing was continued for 3 h with the temperature rising to about 130° C. After the reaction was complete, acrylonitrile was stripped under reduced pressure and the residue purified by column chromatography to afford the pure product 3-(3-chlorophenylamino)propanenitrile (8 g, yield 67%). 1HNMR δ 2.6 (m, 2H), 3.5 (m, 2H), 4.1 (m, 1H), 6.45 (m, 1H), 6.55 (m, 1H), 7.1 (m, 1H).

Workup

  1. temperatureRefluxing
  2. customrising to about 130° C
  3. customthe residue purified by column chromatography

Sources & evidence

ORD record
ord-1c8f6557f8bb427a8367e037774dd661
Source dataset
uspto-grants-2012_01
Patent number
US08106221B2

Reaction notes

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