One-pot Reduction of Nitrostyrenes to Phenethylamines using Sodium Borohydride and Copper(II) chloride

20 September 2023, Version 4
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

The preparation of phenethylamines and phenylisoproylamines of scientific relevance can be achieved with a NaBH4/CuCl2 system in 10 to 30 minutes via reduction of substituted β-nitrostyrenes. The method also reduces nitrobenzene and methyl benzoate in 92 to 97% yields, respectively, while has no effect on benzoic acid, benzamide, and aromatic halides. This one-pot procedure allows the isolation of substituted β-nitrostyrene scaffolds up to 83% yield under mild conditions, without the need for special precautions, inert atmosphere, and time-consuming purification techniques.

Keywords

phenethylamine
sodium borohydride
beta nitrostyrene
2C-X
DOX
reduction
NaBH4
CuCl2
copper chloride
amphetamine

Supplementary materials

Title
Description
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Supporting information
Description
Collection of NMR spectra of all the synthesized products
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