Hantzsch ester

Hantzsch ester refers to an organic compound with the formula HN(MeC=C(CO2Et))2CH2 where Me = methyl (CH3) and Et = ethyl (C2H5).

The compound is a hydride donor, e.g., for reduction of imines to amines.

It is a synthetic analogue of NADH, a naturally occurring dihydropyridine.

[1] Hantzsch ester can be made with a Hantzsch pyridine synthesis where formaldehyde, two equivalents of ethyl acetoacetate and ammonium acetate are combined to afford the product in high yield.

[2] As confirmed by X-ray crystallography, Hantzsch ester has a planar C5N core.

Hantzsch reaction with ammonium acetate, ethyl acetoacetate, formaldehyde and ferric chloride
Hantzsch reaction with ammonium acetate, ethyl acetoacetate, formaldehyde and ferric chloride