双醋瑞因的合成新方法

A Novel Synthetic Method for Diacerein

本研究报道了一条经济、绿色的工艺路线合成双醋瑞因(1)。1,8-二羟基-3-羟甲基-9,10-蒽醌(2)经2-碘酰基苯甲酸氧化,高收率(90%)得到4,5-二羟基-9,10-蒽醌-2-甲醛(3);再以DMSO为溶剂,经Pinnick氧化反应得4,5-二羟基-9,10-蒽醌-2-羧酸(4),收率85%;4在酸性条件下乙酰化得1,总收率54.2%(以2计),纯度99.77%。本工艺不仅避免了重金属残留的问题,革除了易燃易爆氧化试剂的使用,且反应条件温和、操作简便,更适合工业生产的需求。本路线中由2制备4的方法未见文献报道。

An economical and green synthetic process for diacerein （1） was reported. 1,8-Dihydroxy-3- hydroxymethyl-9,10-anthracenedione （2） reacted with 2-iodylbenzoic acid with mild condition via oxidation to give 4,5-dihydroxy-9,10-anthracenedione-2-carbaldehyde （3） in a high yield of 90%. After a Pinnick oxidation in DMSO, 4,5-dihydroxy-9,10-anthracenedione-2-carboxylic acid （4） was obtained with a yield of 85 % . Then 4 was subjected to acetylation in acidic condition to afford the target compound 1 with a purity of 99.77 % and a total yield of 54.2 % （based on 2）. This process avoids the heavy metal residue problem, get rid of the use of flammable and explosive oxidizing reagent, and has mild reaction conditions and simple operation. It is more suitable for industrial production. The synthetic method for compound 4 from compound 2 has not yet been reported in literature.