4-氯-6-硝基喹唑啉主要作为医药合成中间体,用于制备各类含喹唑啉结构的药物分子,在抗疟、抗肿瘤等药物研发中具有重要应用。
医药中间体
合成路线 1(1. 合成:19815-16-8)
产率:93.5%
合成条件:at 90℃; for 3 h;
实验步骤:将4-羟基-6-硝基喹唑啉(化合物5)(3.8g,0.02mol)置于100ml烧瓶中,缓慢加入40ml亚硫酰氯和1ml N,N-二甲基甲酰胺。 将混合物加热至90℃,使固体完全溶解,反应进行3小时(此时发现检测完全),减压蒸发亚硫酰氯,得到棕色固体4 - 氯-6-硝基喹唑啉(化合物6)3.92。 g,产率93.5%,HPLC纯度99.67%。 HNMR(300MHz,CDCl3)89.56(s,1H),8.39(d,J = 1.5Hz 1H),8.76(d,J = 1.5Hz,J = 6.0Hz,1H),8.77(d,J = 6.0Hz,1H)。
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合成路线 2(2. 合成:19815-16-8)
产率:87.2%
合成条件:at 160℃; for 3 h;
实验步骤:步骤14-氯-6-硝基 - 喹唑啉-6-硝基-3H-喹唑啉-4-酮4a(18.88g,99.40mmol)溶解在磷酰氯(31.03g,149mmol)中。将混合物温热至160℃。 搅拌3小时。将反应混合物加入250mL正己烷中,同时加热,搅拌,从溶液中沉淀出大量固体,过滤,用正己烷洗涤滤饼,真空干燥。 得到标题化合物4-氯-6-硝基 - 喹唑啉4b(18.14g,收率87.2%),为黄色固体。
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