摘要
目的合成抗抑郁药西酞普兰中间体5-溴苯酞。方法以4-硝基邻苯二甲酰亚胺为原料,通过铁粉还原得4-氨基邻苯二甲酰亚胺,再经锌粉还原排氨得到5-氨基苯并呋喃-1-酮,最后经重氮化、溴代得5-溴苯酞,利用红外光谱确证结构。结果对各步反应条件进行考察,得出各步反应的最佳条件。结论本合成路线简便可行,原材料价廉易得,适合工业化生产。
Abstract
OBJECTIVE To synthesis 5-bromide benzofuran ketone,the key intermediate of citaopram. METHODS The target compound was prepared through reduction of 4-nitrophthalic imidine,discharging amine with zinc powder,diazotization and bromination. The products were characterized by FT-IR.RESULTS All the influent factors to each step have been discussed respectively,and the optimization condition have been obtained.CONCLUSION The synthesis route is convenient. Raw and processed materials are low-cost,and the process may be used in industry.
关键词
还原 /
溴化 /
重氮化 /
5-溴苯酞
{{custom_keyword}} /
Key words
reduction /
bromination /
diazotization /
5-bromide benzofuran ketone /
citalopram
{{custom_keyword}} /
吕亮;吾国强.
抗抑郁药西酞普兰中间体5-溴苯酞的合成[J]. 中国药学杂志, 2006, 41(24): 1905-1908
Lü Ling;WU Guo-qing.
Synthesis of 5-Bromide Benzofuran Ketone as Intermediate of Citalopram [J]. Chinese Pharmaceutical Journal, 2006, 41(24): 1905-1908
{{custom_sec.title}}
{{custom_sec.title}}
{{custom_sec.content}}
参考文献
[1] LIN K. Survey of research on Citalopram [J] .Eval Anal Druguse Hosp China (中国医院用药评价与分析)，2003，3 (5)： 319-320.
[2] YU H X，GUO F. Graphical synthetic routes of Citalopram [J] .Chin J Pharm (中国医药工业杂志)，2003，(10)： 535-536.
[3] PETERSEN H，AHMADIAN H，DANCER R. Method for the preparation of Citalopram [P] . CN 1339436. 2002-03-13.
[4] PETERSEN H，DAICEL R. Method for the preparation of Citalopram [P] . CN 1441795. 2003-09-10.
[5] PETERSEN H，DAHLBERG N P. Preparation of 5-cyanophthalide [P] . CN 1331686. 2002-01-16.
[6] YU H X，GUO F. Improved synthesis of 5-bromoisobenzofuran-1(3H)-one[J] .Chin J Med Chem(中国药物化学杂志)，2002，12 (6)： 352-353.
[7] ZHOU X L. Medicament(药物)[M] . Beijing，Chemical Industry Press.2003.
[8] FAN N T. Dictionary of Organic Synthesis(有机合成事典)[M] . Bejing，Beijing Institute of Technology Press.1992.
[9] BOGERT M T，RENSHAW R R. 4-Amino-o-phthalic acid and some of its derivatives [J] .J Am Chem Soc，1908，30 (7)： 1135-1144.
[10] JEAN T. 5-substitued phthalides [J] .Bull Soc Sci Bretagne Spect，1951，26 (1)： 35-43.
{{custom_fnGroup.title_cn}}
脚注
{{custom_fn.content}}
