Hantzsch ester

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Hantzsch ester
HantzschEster.svg
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 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 214-561-6
PubChem CID
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
Appearancecolorless 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, formaldehyde and ferric chloride Hantzsch pyridine synthesis.svg
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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