合成路线:The bromination of 3,4-dihydro-1H-2-benzopyran (VII) with Br2 gives the 1-bromo derivative (VIII),which,without isolation,is treated with hot HBr yielding 2-(2-bromoethyl)benzaldehyde (IX).The condensation of (IX) with nitromethane in acidic medium affords the nitrostyrene (X),which is cyclized with treatment with FeCl3 and acetyl chloride giving 4-(2-bromoethyl)-3-chloroindolin-2-one (XI).The dechlorination of (XI) with NaH2PO2 over Pd/C yields 4-(2-bromoethyl)indolin-2-one (XII),which is finally condensed with dipropylamine (II).
合成路线:The reaction of 3,4-dihydro-1H-2-benzopyran (VII) with benzoyl chloride and ZnCl2 gives benzoic acid 2-[2-(chloromethyl)phenyl]ethyl ester (XIII),which is condensed with hexamethylenetetramine (XIV) yielding the amminium salt (XV).The hydrolysis of (XV) affords 2-(2-benzoyloxyethyl) benzaldehyde (XVI),which is condensed with nitromethane as before to give the nitrostyrene (XVII).The cyclization of (XVII) with FeCl3 and acetyl chloride as before yields 4-(2-benzoyloxyethyl)-3-chloroindolin-2-one (XVIII),which is dechlorinated with hydrazine and Pd/C to the indolinone (XIX).The hydrolysis of (XIX) with NaOH affords 4-(2-hydroxyethyl)indolin-2-one (XX),which is acylated with TsCl giving the tosylate (XXI).Finally,this compound is condensed with dipropylamine (II).
参考文献标题:Development of large-scale syntheses or ropinirole in the pursuit of a manufacturing process
文献作者:Hayler,J.D.; et al.
参考来源:Org Process Res Dev 1998,2(1),3
产品链接: CAS No. 91374-20-8›› 产品链接: CAS No.91374-21-9››