An improved synthetic process for 3-benzyloxy-4-n-butylaniline hydrochloride the key intermediate of nequinate which is an anticoccidal drug to parasites of Eimeria,was described.The process was started with 3-aminoph...An improved synthetic process for 3-benzyloxy-4-n-butylaniline hydrochloride the key intermediate of nequinate which is an anticoccidal drug to parasites of Eimeria,was described.The process was started with 3-aminophenol,via acylation,Fries rearrangement,benzylation,hydrolysis,and Huang-Minlon reduction,to give the title compound.The optimal reaction conditions and molar yield were as follows:acylation,130—140℃ for 3 h;Fries rearrangement,140℃ for 5 h,77.9%(based on 3-aminophenol);benzylation,70℃ for 2 h and 80℃ for 4 h,81.3%;hydrolysis and Huang-Minlon reduction,reflux for 90 min,78.2%.The structures of the main compounds were confirmed by 1H NMR.The process is much of industrial value because of high yields,cheap and available materials,moderate reaction conditions and convenient operations.展开更多
文摘An improved synthetic process for 3-benzyloxy-4-n-butylaniline hydrochloride the key intermediate of nequinate which is an anticoccidal drug to parasites of Eimeria,was described.The process was started with 3-aminophenol,via acylation,Fries rearrangement,benzylation,hydrolysis,and Huang-Minlon reduction,to give the title compound.The optimal reaction conditions and molar yield were as follows:acylation,130—140℃ for 3 h;Fries rearrangement,140℃ for 5 h,77.9%(based on 3-aminophenol);benzylation,70℃ for 2 h and 80℃ for 4 h,81.3%;hydrolysis and Huang-Minlon reduction,reflux for 90 min,78.2%.The structures of the main compounds were confirmed by 1H NMR.The process is much of industrial value because of high yields,cheap and available materials,moderate reaction conditions and convenient operations.
