Study on electrocarboxylation of [(4-methoxy-benzylidene)-amino]-acetic acid ester

In an undivided cell, the electrocarboxylation of [(4-methoxy-benzylidene)-amino] - acetic acid ester bearing an aliphatic substituent on the amine fragment was first investigated in the DMF solution under the atmospheric pressure of carbon dioxide using magnesium rod as the sacrificial anode. As a result, C-carboxylated, N-carboxylated and C,N-dicarboxylated products were isolated as their methyl esters whose yields were influenced by various reaction conditions including the supporting electrolyte, cathode material, current density, charge passed and temperature. Using glassy carbon as the working electrode, the electrochemical behavior of the aryl alkyl substrate was studied by cyclic voltammetry. Based on the character in the absence and presence of carbon dioxide, the possible electrocarboxylation mechanism was postulated accordingly.