Aniline → trans-Cinnamamide

HRID 1994099Notes

Reaction equation

HRID 1994099 reaction equation
C(O)(=O)C=C.C(Cl)(=O)C(Cl)=O.N[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[C:19]([NH2:23])(=[O:22])[CH:20]=[CH2:21]>[Pd]>[CH:16]1[CH:17]=[CH:18][C:13](/[CH:21]=[CH:20]/[C:19]([NH2:23])=[O:22])=[CH:14][CH:15]=1

Participants

6

Reactant 4

HCID 6115AnilineHCID 6579AcrylamideHCID 6581Acrylic AcidHCID 65578Oxalyl chloride

Product 1

HCID 5273472trans-Cinnamamide

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Acrylic acid vii is converted to the acid chloride with oxalyl chloride, and the resulting acid chloride is reacted with an aniline in the presence of base. The resulting acrylamide viii is then reacted with an appropriately substituted aryl iodide ix in the presence of a palladium catalyst and a base to give the cinnamide vi.

Sources & evidence

ORD record
ord-a9f07c831d5d4cc7b7478445fb8fbec7
Source dataset
uspto-grants-2010_01
Patent number
US07652041B2

Reaction notes

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