Article · Wikipedia archive · Last revised Jun 6, 2026

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.

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Jun 6, 2026
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Hantzsch ester
source ↗
Names
Other names
Diludine, 1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylic acid diethyl ester
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.013.237
EC Number
  • 214-561-6
UNII
  • InChI=1S/C13H19NO4/c1-5-17-12(15)10-7-11(13(16)18-6-2)9(4)14-8(10)3/h14H,5-7H2,1-4H3
    Key: LJXTYJXBORAIHX-UHFFFAOYSA-N
  • CCOC(=O)C1=C(NC(=C(C1)C(=O)OCC)C)C
Properties
C13H19NO4
Molar mass 253.298 g·mol−1
Appearance colorless solid
Melting point 182–183 °C (360–361 °F; 455–456 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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 source ↗

Structure

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

Further reading

Further reading

See also

See also

References

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.