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Hantzsch ester

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Hantzsch ester
Names
Other names
Diludine, 1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylic acid diethyl ester
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard100.013.237Edit this at Wikidata
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 mass253.298 g·mol−1
Appearancecolorless solid
Melting point182–183 °C (360–361 °F; 455–456 K)
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
Chemical compound

Hantzsch ester refers to anorganic 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 a1,4-dihydropyridine. It is named afterArthur Rudolf Hantzsch who described its synthesis in 1881. The compound is a hydride donor, e.g., for reduction ofimines toamines. It is a synthetic analogue ofNADH, a naturally occurring dihydropyridine.[1]

Preparation

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Hantzsch ester can be made with aHantzsch pyridine synthesis whereformaldehyde, two equivalents ofethyl acetoacetate andammonium 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

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

Further reading

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See also

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References

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  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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