Aniline → HCID 178469510, compound

Participants

Reaction Steps

The intermediates (1) are prepared according to the procedures described in J. Amer Chem. Soc. 68, 1204 (1946). Ethoxymethylenemalonate is warmed with an appropriate aniline to give an anil which cyclizes upon heating in boiling diphenylether to give the ethyl-4-hydroxyquinoline-3-carboxylate. Reaction of this intermediate with phosphorus oxychloride gives the intermediate (1). The intermediates (2) are either commercially available or can be prepared from the corresponding ester by hydrolysis. The intermediate (3) can be prepared from (6) by ##STR11## treatment with hydroxylamine hydrochloride followed by reduction of the oxime with nickle/aluminum alloy as described in U.S. Pat. No. 3,875,163, or, when a weaker reducing agent is required, by treatment with ammonium acetate followed by reduction with sodium cyanoborohydride as described in J. Amer. Chem. Soc., 68, 7032 (1979). The intermediate (6) can be prepared. as described in U.S. Pat. No. 4,816,464. The intermediate R8NHR17 where R17 is ##STR12## and R8 is not H can be prepared from (3) by acylation with R15COCl or (R15CO)2O or formylation with formic acetic anhydride followed by reduction with lithium aluminum hydride.

Provenance & Evidence