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Transformations of 1-(2-Aminophenyl)propan-2-ol to 2-Methylindoline

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Abstract

The transformation reaction of 1-(2-aminophenyl)propan-2-ol was studied at 200 °C under argon pressure. A range of catalysts was applied including carbon, titania and zeolite supported Ru, Pd, Pt, Rh, and Ir, as well as metal free zeolites. The highest conversion was obtained with H-Beta-150 and H-Beta-25 and the highest selectivity to 2-methylindoline was achieved with 0.3 % Ir–H-Beta-150 and H-Beta-25. Although the selectivity to 2-methylindole was high for all catalysts, formation of the final product 2-methylindoline only took place over the most acidic catalysts.

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Acknowledgments

This work is a part of activities at the Åbo Akademi Process Chemistry Centre (PCC), a Centre of Excellence financed by Åbo Akademi University. Financial support from European Union through the Seventh Framework Programme (Project 246095-2) is gratefully acknowledged. Mr. Markku Reunanen and Dr. Annika Smeds are acknowledged for analysis by GC–MS.

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Authors and Affiliations

  1. Laboratory of Industrial Chemistry and Reaction Engineering, Process Chemistry Centre, Åbo Akademi University, Biskopsgatan 8, 20500, Turku, Finland

    Heidi Bernas, Atte Aho, Narendra Kumar & Dmitry Yu. Murzin

  2. Boreskov Institute of Catalysis, 630090, Novosibirsk, Russia

    Yuliya S. Demidova & Irina L. Simakova

  3. Novosibirsk State University, 630090, Novosibirsk, Russia

    Yuliya S. Demidova & Irina L. Simakova

  4. Sanofi-Aventis Recherche & Developpement, Centre de Recherche de Vitry-sur-Seine 13, quai Jules Guesde, BP 14, 94403, Vitry-sur-Seine, France

    Yosra Laribi & Philippe Perrichon

  5. Laboratory of Organic Chemistry, Åbo Akademi University, Biskopsgatan 8, 20500, Turku, Finland

    Reko Leino

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  1. Heidi Bernas
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  2. Yuliya S. Demidova
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  9. Dmitry Yu. Murzin
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Corresponding author

Correspondence to Dmitry Yu. Murzin.

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Bernas, H., Demidova, Y.S., Aho, A. et al. Transformations of 1-(2-Aminophenyl)propan-2-ol to 2-Methylindoline. Catal Lett 145, 955–963 (2015). https://doi.org/10.1007/s10562-014-1474-3

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  • DOI: https://doi.org/10.1007/s10562-014-1474-3

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