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Photocatalytic Selective Reduction by TiO2 of 5-Nitrosalicylic Acid Ethyl Ester: A Mild Route to Mesalazine

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Abstract

Photoexcited TiO2 dispersed in a de-aerated acetonitrile/2-propanol (CH3CN/2-PrOH) reaction mixture catalyzes the quick and selective reduction of 5-nitrosalicylic acid methyl ester to the corresponding aniline, an immediate precursor of the drug mesalazine. The transformation is selective also when the starting concentration of nitro compound is increased by orders of magnitude and occurs at room temperature and atmospheric pressure. The photocatalyst can be reused. The photocatalytic reaction can be carried out also under aerated conditions without any loss in selectivity and efficiency. All these factors point out the feasibility of this important synthesis under mild conditions.

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Acknowledgements

A special acknowledgment goes to Dr. Rossano Amadelli for his valuable contribution to the scientific discussion and development of the research.

Funding

We thank University of Ferrara (FAR 2017–2018) for funding.

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Authors and Affiliations

  1. Dipartimento di Scienze Chimiche e Farmaceutiche, Università degli Studi di Ferrara, Via Luigi Borsari 46, 44121, Ferrara, Italy

    A. Molinari, M. Mazzanti & M. Fogagnolo

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  1. A. Molinari
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  2. M. Mazzanti
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  3. M. Fogagnolo
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Correspondence to A. Molinari.

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Molinari, A., Mazzanti, M. & Fogagnolo, M. Photocatalytic Selective Reduction by TiO2 of 5-Nitrosalicylic Acid Ethyl Ester: A Mild Route to Mesalazine. Catal Lett 150, 1072–1080 (2020). https://doi.org/10.1007/s10562-019-02993-3

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  • DOI: https://doi.org/10.1007/s10562-019-02993-3

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