Acrylonitrile → 2-Methyl-5-nitrocinnamonitrile

HRID 1156473

Reaction equation

HRID 1156473 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:3]=1[C:4](Cl)=O.[C:14](#[N:17])[CH:15]=C.C(C(CCCC)CN(CC(CC)CCCC)CC(CC)CCCC)C>C1(=O)CCCC1>[CH3:1][C:2]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:3]=1[CH:4]=[CH:15][C:14]#[N:17]

Participants

5

Reactant 3

HCID 7855AcrylonitrileHCID 102705Tri(2-ethylhexyl)amineHCID 44365682-Methyl-5-nitrobenzoyl chloride

Product 1

HCID 541228552-Methyl-5-nitrocinnamonitrileYield 24%

Reagents, catalysts & solvents 1

HCID 8452CyclopentanoneSolvent

Procedure

0.2877 g (0.5 millimol) of bis-(dibenzylideneacetone)-palladium(O), 9.98 g (50 millimols) of 2-methyl-5-nitrobenzoyl chloride, 3.31 g (62.5 millimols) of acrylonitrile and 17.68 g (50 millimols) of tris-(2-ethylhexyl)-amine, in 100 ml of cyclopentanone, are stirred for 1.5 hours at 100° C. The crude product is chromatographed on silica gel, in methylene chloride, and is then recrystallised from cyclohexane/carbon tetrachloride. 2.1 g (24% of theory) of 2-methyl-5-nitrocinnamonitrile are obtained in the form of white crystals; melting point 113.2° C.

Workup

  1. customThe crude product is chromatographed on silica gel, in methylene chloride
  2. customis then recrystallised from cyclohexane/carbon tetrachloride

Sources & evidence

ORD record
ord-acf01ee7b42f4c8cabb18159f2455709
Source dataset
uspto-grants-1982_06
Patent number
US04335054

Linked notes

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