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CC BY 4.0 · Pharmaceutical Fronts 2022; 04(03): e151-e156
DOI: 10.1055/s-0042-1756457
Original Article

Selective Nitro Reduction of Ester Substituted Nitroarenes by NaBH4-FeCl2

Zi-Hong Zhou
1   Department of Process Research and Development, HEC Pharm Group, Dongguan, People's Republic of China
2   School of Biology and Biological Engineering, South China University of Technology, Guangzhou, People's Republic of China
,
Yong-Bo Xu
1   Department of Process Research and Development, HEC Pharm Group, Dongguan, People's Republic of China
,
Shu-Ming Wu
1   Department of Process Research and Development, HEC Pharm Group, Dongguan, People's Republic of China
3   State Key Laboratory of Anti-Infective Drug Development, Sunshine Lake Pharma Co., Ltd., Dongguan, People's Republic of China
,
Wei-Jian Ling
1   Department of Process Research and Development, HEC Pharm Group, Dongguan, People's Republic of China
,
Lei Zhang
2   School of Biology and Biological Engineering, South China University of Technology, Guangzhou, People's Republic of China
,
Zhong-Qing Wang
1   Department of Process Research and Development, HEC Pharm Group, Dongguan, People's Republic of China
3   State Key Laboratory of Anti-Infective Drug Development, Sunshine Lake Pharma Co., Ltd., Dongguan, People's Republic of China
4   School of Pharmacy, Xiangnan University, Chenzhou, People's Republic of China
› Author Affiliations Funding This work was supported by the State Key Laboratory of Anti-Infective Drug Development (Sunshine Lake Pharma Co., Ltd) with Grant No. 2015DQ780357 and Guangdong Basic and Applied Basic Research Foundation (Grant No. 2020A1515110131).
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Abstract

This work aimed to explore a novel protocol for selective reduction of the nitro group on the aromatic ring while remaining the ester group unaffected. In this study, NaBH4-FeCl2 was disclosed as a key reductant in the process. NaBH4-FeCl2-mediated reduction showed high chemoselectivity, gave the desired products in magnificent yield (up to 96%), and was applied to synthesize a key intermediate of vilazodone (an antidepressant drug) on a hectogram scale in a total yield of 81% (two steps). The protocol is practical, and capable of synthesis of a range of aromatic amines, especially those with ester substituted in the ring.

Keywords

ester - nitroarene - selectivity reduction - sodium borohydride - vilazodone

Supplementary Material



Publication History

Received: 13 May 2022

Accepted: 06 August 2022

Article published online:
19 September 2022

© 2022. The Author(s). This is an open access article published by Thieme under the terms of the Creative Commons Attribution License, permitting unrestricted use, distribution, and reproduction so long as the original work is properly cited. (https://creativecommons.org/licenses/by/4.0/)

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