Knoevenagel Condensation

Mechanism of the Knoevenagel Condensation

Original publication	Ber. Dtsch. Chem. Ges.. 1898, 31, 2596. Z. Naturforsch.. 1986, 41b, 371.
Reviews	Curr. Org. Chem.. 2012, 9, 31. Org. React.. 1967, 15, 204.

Sample reactions

Et2NH, H2C(CN)2

EtOH

50 to 100 °C, 10 min, 95-98%

Et2NH, H2C(CN)2

EtOH

100 °C, 60 min, 97%

Malonic Acid, PhNH2

EtOH

Reflux, 8 h, 70-75%

"The starting material is an intermediate of the second part of this synthesis."

(CH2NH2)2.2AcOH

PhH

RT, 2 h

NaOMe

MeOH

0 °C, 30 min

NaOMe

MeOH

0 °C, 2 h, 47% (5 steps)

Piperidine

EtOH

Reflux, 60 min, 81%

H2O