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Diethyl aminomalonate hydrochloride

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Diethyl aminomalonate hydrochloride Basic information

Product Name:
Diethyl aminomalonate hydrochloride
Synonyms:
  • AMino Malonic diethyl ester hydrochloride
  • aminomalonate hydrochloride
  • Diethyl 2-aminopropanedioate hydrochloride
  • 1,3-diethyl 2-aminopropanedioate, HCl
  • Diethyl aMinoMalonate hydrochloride (AMinoMalonaMid)
  • Aminomalonamid
  • Diethyl 2-aminomalonate hydrochloride 99%
  • Diethyl aminomalonat
CAS:
13433-00-6
MF:
C7H14ClNO4
MW:
211.64
EINECS:
236-556-8
Product Categories:
  • Building Blocks
  • C6 to C7
  • Carbonyl Compounds
  • Chemical Synthesis
  • Esters
  • Organic Building Blocks
  • Pharmaceutical Intermediates
  • Small molecule
  • API intermediates
  • bc0001
  • 13433-00-6
Mol File:
13433-00-6.mol
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Diethyl aminomalonate hydrochloride Chemical Properties

Melting point:
165-170 °C (dec.)(lit.)
storage temp. 
Inert atmosphere,2-8°C
solubility 
Chloroform, DMSO, Water
form 
Crystalline Powder
color 
White to slightly yellow
Water Solubility 
soluble
Sensitive 
Hygroscopic
BRN 
3568037
InChIKey
GLFVNTDRBTZJIY-UHFFFAOYSA-N
CAS DataBase Reference
13433-00-6(CAS DataBase Reference)
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Safety Information

Hazard Codes 
Xi
Risk Statements 
36/37/38
Safety Statements 
26-36
WGK Germany 
3
Hazard Note 
Irritant
HS Code 
29224995

MSDS

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Diethyl aminomalonate hydrochloride Usage And Synthesis

Chemical Properties

white to slightly yellow crystalline powder

Uses

Diethyl aminomalonate hydrochloride is used as a pharmaceutical intermediate. Diethyl aminomalonate with formaldehyde generates an azomethine ylide which can undergo cycloadditions with 1,2-dipolarophiles to form pyrrolidines.

Synthesis

A solution of 420.0 g of a mixture of diethyl hydroxyiminomalonate and diethyl acetoxyiminomalonate (together 2.0 mol) in 400 ml of ethyl acetate, 40.0 g of anhydrous magnesium sulfate and 12.5 g of palladium on activated charcoal (5 percent by weight of Pd) as hydrogenation catalyst were placed in a 1.5 l pressure reactor equipped with a stirrer. At 30° to 35° C., hydrogen was introduced under a pressure of 20 bar for 80 minutes until the pressure remained constant. The reactor contents were thoroughly mixed by stirring during this process. The hydrogenation mixture was cooled to 20° C. and diluted with 200 ml of ethyl acetate and the mixture of hydrous magnesium sulfate and catalyst was filtered off. The solid which had been separated off was washed three times with a total of 200 ml of ethyl acetate and the wash liquor was combined with the filtrate. Diethyl aminomalonate hydrochloride was precipitated out as a white solid by the introduction of 68 g of dry hydrogen chloride, filtered off, washed with ethyl acetate and dried under a water jet vacuum at 70° C. The yield was 359.6 g (85.1% of theory), the melting point was 165° C. and the purity according to the analytically determined chlorine content was 100%.

Diethyl aminomalonate hydrochlorideSupplier

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