Acrylamide → 3-(4-Amino-3,5-dimethylphenyl)-2-propenenitrile

HRID 1847134Notes

Reaction equation

HRID 1847134 reaction equation
Br[C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([NH2:9])=[C:4]([CH3:10])[CH:3]=1.[C:11]([NH2:15])(=O)[CH:12]=[CH2:13].CC1C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.P(Cl)(Cl)(Cl)=O>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(N(CC)CC)C>[C:11]([CH:12]=[CH:13][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([NH2:9])=[C:4]([CH3:10])[CH:3]=1)#[N:15]

Participants

7

Reactant 4

HCID 6579AcrylamideHCID 24813Phosphorus oxychlorideHCID 80271Tri-o-tolylphosphineHCID 905494-Bromo-2,6-xylidine

Product 1

HCID 573502333-(4-Amino-3,5-dimethylphenyl)-2-propenenitrileYield 67%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 8471TriethylamineSolvent

Procedure

The third route disclosed in WO 03/016306 involved reaction of 4-bromo-2,6-dimethylphenylamine with acrylamide in presence of palladium acetate, tris(2-methylphenyl)phosphine and N,N-diethylethanamine. The resulting amide was dehydrated using phosphoryl chloride to give 4-(2-cyanoethenyl)-2,6-dimethylphenylamine in a moderate yield of 67% without mentioning the E/Z ratio.

Sources & evidence

ORD record
ord-6caf65c909424b25887d3bbd84f14953
Source dataset
uspto-grants-2015_02
Patent number
US08952155B2

Reaction notes

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