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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). 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.

Hantzsch reaction with ammonium acetate, ethyl acetoacetate, and formaldehyde

Structure

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

References

(2020). "Encyclopedia of Reagents for Organic Synthesis".
(2010). "Rapid and Convenient Synthesis of the 1,4-Dihydropyridine Privileged Structure". Journal of Chemical Education.
(2015). "On-Column Reaction Set-Up for High-Throughput Screenings and Mechanistic Investigations". Advanced Synthesis & Catalysis.

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dihydropyridines substances-discovered-in-the-19th-century

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