| 第 35 卷第 4 期 |  | Vol. 35 No. 4 | | 2005 年 8 月 | Aug 2005 |
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所屬欄目：醫藥及中間體
6-甲氧基-5-氰基異喹啉的合成研究 |
| 陳有剛; 周新銳(大連理工大學(xué)精細化工國家重點(diǎn)實(shí)驗室; 大連遼寧11602) |
| 摘 要：以間甲氧基苯甲醛為起始原料,20℃下與硝基甲烷反應2h得到3-甲氧基-β-硝基苯乙烯,收率88%。氫化鋁鋰為還原劑,無(wú)水四氫呋喃作溶劑,室溫條件下反應4h,得到3-甲氧基苯乙胺,收率85.4%。100℃條件下,先與甲醛水溶液反應,再與20%鹽酸反應得到6-甲氧基四氫異喹啉,收率80%。在RaneyNi作用下,190℃反應5h脫氫得到6-甲氧基異喹啉,收率86.5%。然后濃硫酸介質(zhì)中,N-溴代丁二酸亞胺作用下,-5℃反應5h得到6-甲氧基-5-溴代異喹啉,收率93%。無(wú)水二甲基亞砜溶劑,氰化亞銅190℃反應2h氰解得到5-氰基-6-甲氧基異喹啉,收率95%。該化合物是一種重要的藥物中間體和染料中間體,產(chǎn)品經(jīng)過(guò)核磁共振和紅外光譜檢驗確定結構。 |
| 關(guān)鍵詞：間甲氧基苯甲醛; 3-甲氧基-β-硝基苯乙烯; 3-甲氧基苯乙胺; 6-甲氧基四氫異喹啉; 6-甲氧基異喹啉; 6-甲氧基-5-氰基異喹啉 |
| 中圖分類(lèi)號：TQ253.23 文獻標識碼：A 文章編號：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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