1958 年 78 巻 4 号 p. 428-431
Local anesthetics of alkoxynaphthylamine derivatives, having a dialkylaminoacyl group, had been synthesized from 2-naphthol. In the present series of work, 1-alkoxy-4-dialkylaminoacylamidonaphthalene hydrochlorides were synthesized starting with 2-naphthol.
2-Naphthol was nitrated through the alkoxynaphthalenes (alkyl=methyl, ethyl, butyl, isopentyl), reduced to 1-alkoxy-4-aminonaphthalene, and reacted with chloroacetyl chloride, 2-bromopropionyl bromide, or 2-bromobutyryl bromide, in the presence of potassium acetate, in glacial acetic acid, to form 1-alkoxy-4-haloacylamidonaphthalenes. These were reacted with dimethyl- or diethylamine in benzene, by heating in a sealed tube to 100°, and 1-alkoxy-4-dialkylaminoacylamidonaphthalenes were obtained. Passage of dry hydrogen chloride gas through their ether solution afforded the objective compounds, which numbered 24 in all.