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Acta Chimica Sinica ›› 1962, Vol. 28 ›› Issue (3): 155-159. Previous Articles Next Articles
李述文, 高怡生
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LI SHU-WEN, KAO YEE-SHENG
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4-Deoxypyridoxine (Ⅰ) is an effective antagonist of pyridoxine, and also a biochemical reagent.It possesses antitumour effect in pyridoxine-deficient animals.In this investigation a new route for the synthesis of Ⅰ has been described.The starting material is o-aminoacetophenone (Ⅱ), which in turn is obtained from o-nitroethylbenzenc,a by-product in the production of certain drugs.Ⅱ condenses with bromoacetonc in dilute alcohol in the presence of potassium hydroxide to give 2,4-dimethyl-3-hydroxyquinoline (Ⅲ).The latter is ethylated with ethyl iodide to afford 2,4-dimethyl-3-ethoxyquinolinc hydrochloride (Ⅳ), which is then converted to 2,4-dimethyl-3-ethoxypyridine-5,6-dicar-boxylic acid (Ⅷ) via two routes:(1) Ⅳ is oxidized directly with potassium permanganate in aqueous potassium carbonate solution, and (2) Ⅳ is converted to a nitro deriva-five (Ⅴ), then catalytically hydrogenated to an amino compound and finally oxidized to Ⅶ by potassium permanganate.VII is decarboxylated and then estcriEied with diazomc-thane to give the corresponding methyl ester (Ⅸ).Upon reduction with lithium aluminium hydride the ester is converted to 2,4-dimethyl-3-ethoxy-5-hydroxymethylpyridinc hydrochloride (Ⅹ) which upon treating with dilute hydrochloric acid in a sealed tube at 200-205°, yields the desired product (Ⅰ).
LI SHU-WEN, KAO YEE-SHENG. A NEW SYNTHESIS OF 4-DEOXYPYRIDOXINE[J]. Acta Chimica Sinica, 1962, 28(3): 155-159.
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