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, 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

Publikationsverlauf

Eingereicht: 13. Mai 2022

Angenommen: 06. August 2022

Artikel online veröffentlicht:
19. September 2022

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