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Acta Chimica Sinica ›› 1962, Vol. 28 ›› Issue (3): 160-166. Previous Articles Next Articles
李述文, 高怡生
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LI SHU-WEN, KAO YEE-SHENG
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In the present investigation 2-methyl-3-hydroxymethyl-5-nitrophenol (Ⅴ), which may be regarded as a ring analogue of deoxypyridoxine, was synthesized for the purpose of casting its antagonistic action against pyridoxine activity and inhibiting action on the growth of tumours.The starting material was 2-methyl-5-nitrobenzyl chloride (Ⅵ).It was nitrated to give 2-methyl-3,5-dinitrobenzyl chloride (Ⅶ), which on acet5lation was converted to 2-methyl-3,5-dinitrobenzyl acetate (Ⅷ).The latter was reduced with stannous chloride in a mixed solvent of alcohol and acetic acid to yield 2-methyl-3-amino-5-nitrobenzyl acetate (Ⅹ), which was then diazotized and hydrolysed to give the desired product (Ⅴ).In order to establish the position of the amino group, compound Ⅹ was subjected to deamination and then converted to 2-metyl-5-nitrobenzyl alcohol (ⅩⅠ).The latter gave no depression of melting point when admixed with an authentic sample prepared from Ⅵ.An attempt to convert the methyl group of V into an aldehyde group by oxidating ⅩⅡ with chromic acid resulted in the oxidation of the methylene insteaU of the methyl group of ⅩⅡ.
LI SHU-WEN, KAO YEE-SHENG. SYNTHESIS OF 2-METHYL-3-HYDROXYMETHYL-5-NITROPHENOL[J]. Acta Chimica Sinica, 1962, 28(3): 160-166.
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