Selective Nitro Reduction of Ester Substituted Nitroarenes by NaBH4-FeCl2

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, NaBH 4 -FeCl 2 was disclosed as a key reductant in the process. NaBH 4 -FeCl 2 -mediated reduction showed high chemoselectiv...

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Bibliographic Details
Published in:Pharmaceutical fronts 2022-09, Vol.4 (3), p.e151-e156
Main Authors: Zhou, Zi-Hong, Xu, Yong-Bo, Wu, Shu-Ming, Ling, Wei-Jian, Zhang, Lei, Wang, Zhong-Qing
Format: Article
Language:English
Subjects:
ester
nitroarene
Original Article
selectivity reduction
sodium borohydride
vilazodone
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Summary: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, NaBH 4 -FeCl 2 was disclosed as a key reductant in the process. NaBH 4 -FeCl 2 -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.
ISSN:2628-5088
2628-5096
DOI:10.1055/s-0042-1756457