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Reduction of hydrobenzamides: a strategy for synthesizing benzylamines

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Abstract

Indirect reductive amination of aromatic aldehydes was studied in this work; aqueous ammonia was used as a nitrogen source. The results showed that aromatic aldehydes’ reaction with aqueous ammonia produced compounds known as hydrobenzamides (N,N´-(phenylmethylene)bis(1-phenylmethanimines), having good yield. The reaction of hydrobenzamides with sodium borohydride reduced both imine and aminal carbons and produced a primary and secondary benzylamine mixture. This article analyses such behaviour and proposes a possible mechanism for explaining such transformation.

Graphical Abstract

The reaction of aromatic aldehydes with aqueous ammonia produced compounds known as hydrobenzamides (N,N´-(phenylmethylene)bis(1-phenylmethanimines). The reaction of hydrobenzamides with sodium borohydride reduced both imine and aminal carbons and produced a primary and secondary benzylamine mixture.

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Acknowledgments

We would like to thank the Universidad Nacional de Colombia for providing financial support (Research Project No. 57632). On behalf of all authors, the corresponding author states that there is no conflict of interest.

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  1. Departamento de Química, Facultad de Ciencias, Universidad Nacional de Colombia-Sede Bogotá, Carrera 30 No. 45-03, 111321, Bogotá, Colombia

    Andrés Gonzalez-Oñate & Rodolfo Quevedo

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  1. Andrés Gonzalez-Oñate
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  2. Rodolfo Quevedo
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Correspondence to Rodolfo Quevedo.

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Gonzalez-Oñate, A., Quevedo, R. Reduction of hydrobenzamides: a strategy for synthesizing benzylamines. J Chem Sci 136, 24 (2024). https://doi.org/10.1007/s12039-024-02259-5

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