Abstract
A novel formaldehyde-mediated condensation reaction of N,N-dialkyl aromatic amines and resonance-stabilized carbon nucleophiles is described. A condensation reaction between N,N-dimethylaniline ( 4 ) and ethyl acetoacetate ( 8 ) in the presence of formaldehyde in acetic acid took place to give 2-(4-dimethylaminobenzyl)-3-oxo butyric acid ethyl ester ( 9 ) together with the dimerization product 7 in 73 and 21% yields, respectively. This condensation reaction was further applied to the synthesis of 4-substituted dialkylaniline derivatives.
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