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Synthesis of 4-(4-dimethylaminophenyl)-2-methyl-1-pyrroline

B. Proksa, D. Uhrín, A. Vadkerti, and Z. Votický

Institute of Chemistry, Centre for Chemical Research, Slovak Academy of Sciences, CS-84238 Bratislava

 

Abstract: Addition of nitromethane to 4-(4-A^7V-dimethylaminophenyl)-3-buten-2-one (II) afforded 4-(4-A^N-dimethylaminophenyl)-5-nitro-2-pentanone; carbonyl group of the latter was protected, the nitro group was reduced with lithium hydridoaluminate and the resulting amine was cyclized to the required 4-(4-A^-dimethylaminophenyl)-2-methyl-l -pyrroline. Addition of further C-acids to the double bond of compound / / is also described; derivatives of cinnamic acid isolated in this process originated by a retrogressive Michael addition.

Full paper in Portable Document Format: 413a413.pdf

 

Chemical Papers 41 (3) 413–420 (1987)

Thursday, July 09, 2020

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