METHYL 3-CYANOPROPIONATE - C&EN Global Enterprise (ACS

Nov 6, 2010 - Publication Date: December 28, 1959. Copyright © 1959 AMERICAN CHEMICAL SOCIETY. ACS Chem. Eng. News Archives. First Page Image...
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METHYL 3-CYANOPROPIONATE Hydrolysis NCCH2CH2COOCH3 + Ba(0H)2 - * · HOOCCH2CH2COOH Succinic Acid

Aminolysis NCCH2CH2COOCH3 4- HOCH2CH2NH2 No

I 0=1

Solvent

; = o

Ν CH2CH2OH N-(2-hydroxyethyl)~succinimide

NH NH II II NCCH2Cri2COOCH3 + H 2 N - C - N H - C — N H 2 NH2 1ST

^ N

H 2 N X ^ N ^ ^CH2CH 2 CN 3-(2,4-diamino-6-s-triazlnyl)propion/tri/e

Reduction NCCH2CH2COOCH3

New intermediate undergoes reactions of both nitrile and ester groups Methyl 3-cyanopropionate (MCP), a new, high-boiling, difunctional intermediate, brings the syntheses of many unusual prod­ ucts into the area of practical chemistry. A few of the more interesting reaction routes possible with MCP are given at the left. MCP also shows unique potential as a polar solvent. Write to Dept. SP-22 for samples, and literature giv­ ing many more reactions of i methyl 3-cyanopropionate. ChemicaL· for Industry

H2 , KI . X >

(Ni)

I

X

N

X

J=sO

I H 2-pyrrolidone

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