(Z)-Ethyl 3-(2,4,6-trimethylanilino)but-2-enoate

Abstract

The title compound, C15H21NO2, was obtained by the reaction of acetoacetate with 2,4,6-trimethylaniline 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 molecular conformation is stabilized by a strong intramolecular N—H...O hydrogen bond. In addition, the N—H group forms a weak intermolecular N—H...O hydrogen bond linking the molecules into centrosymmetric dimers.