Highly Efficient N-Monomethylation of Primary Aryl Amines
Highly Efficient N-Monomethylation of Primary Aryl Amines
复制标题
芳基伯胺的高效 N-单甲基化
DOI：
10.1002/cjoc.200990224
复制
发表时间：
2009-07-01
影响因子：
5.4
通讯作者：
Pike, Victor
中科院分区：
文献类型：
--
作者：
Peng Yiyuan;Liu Hanliang;Pike, Victor
本文报道了一种高效专一性合成N-单甲基芳胺的方法。在干燥的CH 2Cl 2中用乙酸酐和三乙胺处理苯胺，得到相应的乙酰胺。随后在THF中用碘甲烷和NaH将乙酰芳胺N-单甲基化，引入甲基。N-甲基乙酰苯胺在乙二醇中酸水解，高产率地生成相应的N-甲基-N-芳基胺。该方法还用于合成（E）-2-溴-5-（4-甲基氨基苯乙烯基）吡啶，其可用作阿尔茨海默病的淀粉样蛋白成像剂。
A highly efficient method for specific synthesis of N-monomethylarylamines is presented. Anilines were treated with acetic anhydride and triethylamine in dry CH2Cl2 to give the corresponding acetamides. The subsequent N-monomethylation of acetyl aryl amines with methyl iodide and NaH in THF introduced methyl group. Acid hydrolysis of the N-methyl acetanilides in ethylene glycol generated the corresponding N-methyl-N-aryl amines in high yields. This method was also used to synthesize (E)-2-bromo-5-(4-methylaminostyryl)pyridine that may be useful as an amyloid imaging agent for Alzheimer's disease.