6533b86efe1ef96bd12cbd5d

RESEARCH PRODUCT

On the reactions between ethyl benzoylacetate and anisidines

subject

description

4-Hydroxy-7-methoxy-3-[(m-methoxyphenylimino)-phenylmethyl]-2-quinolone (6) was a by-product of the condensation of ethyl benzoylacetate and m-anisidine; no corresponding products were obtained from p- and o-anisidine. From o-anisidine, 2-phenyl-8-methoxy-4-quinolone (1c) was isolated and characterized; the same reaction also gave 2-phenyl-4-o-anisidyl-1-8-methoxy-quinoline (11) and the Schiff base (14) as by-products; the crotonamide (15) also isolated, is a possible intermediate of the cyclization. The direct condensation of anisidines with ethyl benzoylacetate in diphenyl ether and the transformations of some intermediates were studied.