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 InfoCard
 100.013.237 Edit 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 mass 253.298 g·mol−1
Appearance white or 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

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

  • doi:10.1002/cber.18810140214
    .

See also

References

  1. ISBN 978-0471936237
    .
  2. doi:10.1021/ed100171g
    .
  3. doi:10.1002/adsc.201500311
    .
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