| 第 35 卷第 4 期 |  | Vol. 35 No. 4 | | 2005 年 8 月 | Aug 2005 |
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所属栏目：医药及中间体
6-甲氧基-5-氰基异喹啉的合成研究 |
| 陈有刚; 周新锐(大连理工大学精细化工国家重点实验室; 大连辽宁11602) |
| 摘 要：以间甲氧基苯甲醛为起始原料,20℃下与硝基甲烷反应2h得到3-甲氧基-β-硝基苯乙烯,收率88%。氢化铝锂为还原剂,无水四氢呋喃作溶剂,室温条件下反应4h,得到3-甲氧基苯乙胺,收率85.4%。100℃条件下,先与甲醛水溶液反应,再与20%盐酸反应得到6-甲氧基四氢异喹啉,收率80%。在RaneyNi作用下,190℃反应5h脱氢得到6-甲氧基异喹啉,收率86.5%。然后浓硫酸介质中,N-溴代丁二酸亚胺作用下,-5℃反应5h得到6-甲氧基-5-溴代异喹啉,收率93%。无水二甲基亚砜溶剂,氰化亚铜190℃反应2h氰解得到5-氰基-6-甲氧基异喹啉,收率95%。该化合物是一种重要的药物中间体和染料中间体,产品经过核磁共振和红外光谱检验确定结构。 |
| 关键词：间甲氧基苯甲醛; 3-甲氧基-β-硝基苯乙烯; 3-甲氧基苯乙胺; 6-甲氧基四氢异喹啉; 6-甲氧基异喹啉; 6-甲氧基-5-氰基异喹啉 |
| 中图分类号：TQ253.23 文献标识码：A 文章编号：1009-9212(2005)04-0033-03 |
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| Synthesis of 6-Methoxyisoquinoline-5-Carbonitrile |
| CHEN You-gang; ZHOU Xin-rui （State Key Laboratory of Fine Chemicals; Dalian University of Technology; Dalian 116012; China.） |
| Abstract：Condensation of 3-methoxybenzaldehyde with nitromethane at the temperature 20℃resulted in 3-methoxy-β-nitrostyrene with 88% of yield. Reduction with LiAlH4 in the solvent THF at room temperature afforded 3-methoxy-phenethylamine with 85.4% of yield that reacted with formaldehyde and 20% hydrochloric acid through Pictet-Spengler reaction under the temperature of 100℃ to form 6-methoxyterahydroisoquinoline, and its the yield was 80%. Then dehydrogenation in the presence of Raney Ni at 190℃ afforded 6-methoxyi... |
| Key words：3-methoxy-β-nitrostyrene; 6-methoxy-5-bromoisoquinoline; 6-mehoxyisoquinoline-5-carbonitrile; synthesise; 6-Methoxyisoquinoline; 6-Mehoxyisoquinoline-5-Carbonitrile |
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收稿日期：2005-05-18
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