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by | Feb 6, 2018 | Medium Trees

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

Structure

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

Further reading

See also

References

  1. ^ Bechara, William S.; Charette, André B.; Na, Risong; Wang, Wenliang; Zheng, Chao (2020). "Diethyl 1,4‐Dihydro‐2,6‐dimethyl‐3,5‐Pyridinedicarboxylate". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rn01318. ISBN 978-0471936237.
  2. ^ Cheung, Lawrence L. W.; Styler, Sarah A.; Dicks, Andrew P. (2010). "Rapid and Convenient Synthesis of the 1,4-Dihydropyridine Privileged Structure". Journal of Chemical Education. 87 (6): 628–630. Bibcode:2010JChEd..87..628C. doi:10.1021/ed100171g.
  3. ^ Stockinger, Skrollan; Troendlin, Johannes; Rominger, Frank; Trapp, Oliver (2015). "On-Column Reaction Set-Up for High-Throughput Screenings and Mechanistic Investigations". Advanced Synthesis & Catalysis. 357 (16–17): 3513–3520. doi:10.1002/adsc.201500311.
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