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http://dx.doi.org/10.14478/ace.2019.1054

Effects of Steric Hindrance of 2-Hydroxyphenyl Diazonium Derivatives in the Reductive Reaction by Using Sodium Hydrogensulfite  

Kwon, O-Zoon (Knowledge Industry Center)
Kim, Jieun (Knowledge Industry Center)
Park, Se-Min (Knowledge Industry Center)
Kim, Keun-Sik (Knowledge Industry Center)
Yoon, Soon-Do (Department of Chemical and Biomolecular Engineering, Chonnam National University)
Publication Information
Applied Chemistry for Engineering / v.30, no.4, 2019 , pp. 509-511 More about this Journal
Abstract
Hydrazine derivatives used in fine chemicals, pharmaceuticals and cosmetics can be synthesized by reduction reaction from diazonium derivatives. The reduction method using $SnCl_2$ facilitates the reaction conversion, but the use of $SnCl_2$ is limited when residual heavy metals are issued in the final product. For the conversion of protected (2-hydroxyphenyl)diazonium derivatives into its hydrazine derivatives in Ramalin preparation process, the reduction method was developed by using $NaHSO_3$. In this study, the effect of steric hindrance according to the protected 2-hydroxygroupinphenyldiazonium derivatives was found, and linear C1~C5 alkyl groups for the hydroxy protection were preferable during the diazonium reduction reaction. Considering the economical efficiency and industrial production for the preparation of Ramalin, a variety of protecting groups were investigated. As a result, 2-(allyloxyphenyl)hydrazine was obtained with 85% yield and 99.7% purity when the hydroxy protecting group was used as an allyl group that could be easily deprotected.
Keywords
Hydrazine; Reduction; Diazonium; Sodium sulfite; Ramalin;
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