Hantzsch ester

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Hantzsch ester
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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.[1]

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.[2]

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

Structure

As confirmed by X-ray crystallography, Hantzsch ester has a planar C5N core.[3]

Further reading

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See also

References

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