Synthesis Of Aniline-derived Amine N-oxides

Treatment of chronic hepatitis B is a serious challenge to the world. Hepatitis B virus (HBV) can induce serious liver disease. In order to restrain the replication of HBV effectively, chemists are developing all kinds of anti-HBV drugs. On the basis of the previous work in our group, we have designed and synthesized a new kind of compounds as anti-HBV drug candidates.We used methyl benzoate as starting material and synthesized N-methyl-3-(N',N'-dimethylamino)benzamide by nitration, reduction, methylation, a n d a c y l a t i o n . T h e n w e p r e p a r e d N - m e t h y l - N - b e n z y l - 3 - ( N', N'- d i m e t h y l a m i n o ) b e n z a m i d e , N-methyl-N-(3-chlorobenzyl)-3-(N',N'-dimethylamino)benzamide, and N-methyl-N-butyl-3-(N',N'-dime-thylamino)- benzamide by reacting N-methyl-3-(N',N'-dimethyl-amino)benzamide with chloro-methylbenzene, 1-chloro-3-(chloromethyl)benzene, and 1-bromobutane in the presence of KOH in DMSO respectively. These amines were oxidized by H2O2 to the corresponding N-oxides: N-methyl-3-(N',N'-dimethyl-N'-oxideamino)benzamide, N-methyl-N-benzyl-3-(N',N'-dimethyl-N'-oxideamino)benzamide, N-methyl-N-(3-chlorobenzyl)-3-(N',N'-dimethyl-N'-oxideamino)benzamide, and N-methyl-N-butyl-3- (N',N'-dimethyl-N'-oxideamino)-benzamide. The structures of t h e s e c o m p o u n d s w e r e c h a r a c t e r i z e d b y I R a n d 1 H - N M R .