Dinimide hydrochloride, PD-113322, NCS D355263, KU 87

合成路线:Nitration of 1,8-naphthalic anhydride (I) in sulfuric acid at 60 C for 1 h gives 3,6-dinitro-1,8-naphthalic anhydride (II) in 80% yield (m.p.209-211 C from toluene; NMR: in CDCl3 a 9.22,9.27,2 singlet aromatic H),which,on treatment with unsym-N,N-dimethylethylenediamine at room temperature for 30 min,followed by azeotropical removal of water at 140 C for 2 h in refluxing toluene solution and salt conversion with HCl,yields the monohydrochloride salt of dinimide in 62% yield.

参考文献标题:Dinimide hydrochloride
文献作者:Zee-Cheng,R.K.-Y.; Cheng,C.C.
参考来源:Drugs Fut 1986,11(9),737


合成路线:This compound can be obtained by two related ways:1) The reduction of 3-nitronaphthalene-1,8-dicarboxylic acid anhydride (I) with H2 over Pd/C in DMF gives the corresponding 3-amino-anhydride (II),which is then treated with N,N-dimethylethylenediamine in refluxing toluene or ethanol.(2,3)2) The reaction of anhydride (I) with N,N-dimethylethylenediamine as before gives 2-[2-(dimethylamino)ethyl]-5-nitro-1H-benz[d,e]isoquinoline-1,3 (2H)-dione (III),which is reduced with H2 or HCOONH4 (4) over Pd/C ,or with Sn-HCl at 90-100 C.(1)

合成路线:Nitration of 1,8-naphthalic anhydride (I) in sulfuric acid at 60 C for 1 h gives 3,6-dinitro-1,8-naphthalic anhydride (II) in 80% yield (m.p.209-211 C from toluene; NMR: in CDCl3 a 9.22,9.27,2 singlet aromatic H),which,on treatment with unsym-N,N-dimethylethylenediamine at room temperature for 30 min,followed by azeotropical removal of water at 140 C for 2 h in refluxing toluene solution and salt conversion with HCl,yields the monohydrochloride salt of dinimide in 62% yield.
参考文献标题:N-(Aminoalkyl)imide antineoplastic agents.Synthesis and biological activity
文献作者:Zee-Cheng,R.K.Y.; Cheng,C.C.
参考来源:J Med Chem 1985,28(9),1216-22