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Updated: Jun 1, 2026

Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
(Z)-Ethyl 3-(2,4,6-trimethyl-anilino)but-2-enoate
Manuel Amézquita-Valencia1, Simón Hernández-Ortega, G Alejandra Suárez-Ortiz
1Instituto de Química, Universidad Nacional Autónoma de México, Circuito Exterior, Ciudad Universitaria, México 04510, Mexico.
Abstract:
The title compound, C(15)H(21)NO(2), was obtained by the reaction of acetoacetate with 2,4,6-trimethyl-aniline using Mexican bentonitic clay as a catalyst. It crystallizes in the enamine form. The β-enamino ester residue is almost perpendicular to the aromatic ring [dihedral angle = 88.10 (6)°]. The mol-ecular conformation is stabilized by a strong intra-molecular N-H⋯O hydrogen bond. In addition, the N-H group forms a weak inter-molecular N-H⋯O hydrogen bond linking the mol-ecules into centrosymmetric dimers.
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