(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.

(2Z,2′Z)-Diethyl 3,3′-[butane-1,4-diylbis(azanediyl)]bis(but-2-enoate)

“…For the synthesis of -enamino esters, see: Harrad et al (2010); Hegde & Jones (1993); Lue & Greenhill (1997); Katritzky et al (2004); Bartoli et al (1995); Reddy et al (2005). For the structure of related compounds, see: Harrad et al (2011a,b); Amé zquita-Valencia et al (2009). For hydrogen-bond motifs, see: Bernstein et al (1995).…”

(Z)-Ethyl 3-(2,6-diisopropylanilino)but-2-enoate

“…These compounds are used the preparation of key intermediates of pharmaceutical products (Michael et al, 1999), aminoacids (Palmieri & Cimmerelli, 1996), peptides and alkaloids (David et al, 1999). For our work on the synthesis of enaminoesters, see: Amé zquita- Valencia et al (2009). independent and constrained refinement Á max = 0.11 e Å À3 Á min = À0.10 e Å À3 Table 1 Selected Hydrogen-bond geometry (Å , ).…”