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.^[1]

Hantzsch ester

Names
Other names Diludine, 1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylic acid diethyl ester
Identifiers
CAS Number	1149-23-1 Y
3D model (JSmol)	Interactive image
ChemSpider	64013
ECHA InfoCard	100.013.237
EC Number	214-561-6
PubChem CID	70849
UNII	GWN6123BUG
CompTox Dashboard (EPA)	DTXSID80150895
InChI 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
SMILES CCOC(=O)C1=C(NC(=C(C1)C(=O)OCC)C)C
Properties
Chemical formula	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). Infobox references

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

Structure

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

Further reading

• Hantzsch, A. (1881). "Condensationprodukte aus Aldehydammoniak und Ketonartigen Verbindungen". Chemische Berichte. 14 (2): 1637–8. doi:10.1002/cber.18810140214.

See also

• Hantzsch pyrrole synthesis