1-乙基-4-氧-7-甲基-1,8-萘啶-3-羧酸的合成  

The Synthesize of 1-Ethyl-4-Oxy-7-Methyl-1,8-Naphththyridine-3-Carboxylic Acid

作　　者：夏明珠[1] 王风云[1] 杨廷海[2] 雷武[1] 

机构地区：[1]南京理工大学工业化学研究所,南京210094 [2]南京大学化工学院

出　　处：《应用化学》2007年第4期461-464,共4页Chinese Journal of Applied Chemistry

摘　　要：采用2-氨基-6-甲基吡啶和乙氧基亚甲基丙二酸二乙酯为原料进行缩合反应,在2种原料的摩尔比为1∶1.3,反应时间45 min,反应温度130℃的优化条件下得到收率为96%的N-(6-甲基吡啶-2-基)-胺基亚甲基丙二酸二乙酯。在250℃的反应温度下,分别以二苯醚、石蜡油和邻苯二甲酸二乙酯为热载体进行成环反应,得到4-氧-7-甲基-1,8-萘啶-3-羧酸乙酯的收率分别为88.6%、56.3%和61.2%,确定二苯醚为最佳热载体,并发现反应温度对产率的影响最大,原料配比次之,反应时间基本无影响。用碘乙烷、磷酸三乙酯和碳酸二乙酯作乙基化试剂,并在碱性条件下水解酸化,得到1-乙基-4-氧-7-甲基-1,8-萘啶-3-羧酸目标产物,产率分别为92.6%、90.7%和81.2%。研究了每步产物合成的影响因素,比较了采用碳酸二乙酯作乙基化试剂的优缺点。对每步产物进行了光谱表征,并从质谱图对其碎片做了分析。N-（ 6-methyl-2-pyridine）-amino-methylene-diethyl malonate was produced by condensation reaction of 2-amino-6-methyl pyridine with ethoxymethylene diethyl malonate under optimal conditions that n（2-amino-6-methyl pyridine） ： n （ ethoxymethylene diethyl malonate） is 1 ： 1.3, reacting time 45 min and temperature 130℃, the yield of this reaction was 96%, which was 6% higher than that of literature. Then 4-oxy-7-methyl-1,8-naphththyridine-3-carboxylic acetate was synthesized by cyclization reaction in different heat carrier of diphenyl ether, paraffin oil and diethyl phthaltate in 250℃. The yields were 88.6%, 56. 3% and 61.2% respectively. The results show that diphenyl ether is the best heat carrier and reacting temperature has significant influence on production yield, while the ratio of raw materials and reacting time almost has no influence. Finally, 1-ethyl-4-oxy-7-methyl-1,8-naphththyridine-3-carboxylic acid was produced by ethylation reaction using iodoethane, triethyl phosphate and diethyl carbonate and hydrolysis in alkaline condition. The yield of product is 92.6%, 90. 7% and 81.2% respectively. The influencing factors of synthetic reaction were studied and the advantages and disadvantages of using diethyl carbonate as the ethylization reagent were compared. The compounds were characterized with various spectroscopic methods.

关 键 词：乙基氧甲基萘啶羧酸 缩合反应 成环反应 乙基化反应 水解反应 光谱特征 

分 类 号：O621[理学—有机化学] R378[理学—化学]