Hantzsch ester

Hantzsch ester refers to an organic compound with the formula HN₂CH₂ where Me = methyl and Et = ethyl. It is a light yellow solid. The compound is a 1,4-dihydropyridine. It is named after Arthur Rudolf Hantzsch who described its synthesis in 1881. 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.

Preparation

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.

Structure

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