Acrylonitrile → 3-(3-Iodo-phenylamino)-propionitrile

HRID 963410Notes

Reaction equation

HRID 963410 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].[C:9](#[N:12])[CH:10]=[CH2:11]>C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[I:1][C:2]1[CH:3]=[C:4]([NH:5][CH2:11][CH2:10][C:9]#[N:12])[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 7855AcrylonitrileHCID 122713-Iodoaniline

Product 1

HCID 190816343-(3-Iodo-phenylamino)-propionitrileYield 37%

Reagents, catalysts & solvents 1

HCID 8895Cupric acetateCatalyst

Procedure

13at) 4.38 g of 3-iodoaniline, 1.06 g of acrylonitrile and 0.5 g of copper-(II)acetate are mixed and held at 70° for 5 hrs. The mixture is chromatographed on silica gel with ethyl acetate/cyclohexane 1:4 and yields 2.01 g of 3-(3-iodo-phenylamino)-propionitrile as a brown oil. Yield: 37%. Mass spectrum: peak inter alia at m/e : 272 (M+, 50%), 232 (100%); 105 (35%).

Workup

  1. customThe mixture is chromatographed on silica gel with ethyl acetate/cyclohexane 1:4

Sources & evidence

ORD record
ord-c87e1452187a472ab805a0aa8f596f49
Source dataset
uspto-grants-1998_06
Patent number
US05763450

Reaction notes

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