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A convenient synthesis of 4-(2-hydroxyethyl)indolin-2-one, a useful intermediate for the preparation of both dopamine receptor agonists and protein kinase inhibitors

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Abstract

This paper describes a practical approach to the preparation of 4-(2-hydroxyethyl)indolin-2-one, a key intermediate in the synthesis of dopaminergic agonists such as ropinirole—a drug used in the treatment of Parkinson’s disease and restless legs syndrome—and of two sets of protein kinase inhibitors. The sequence starts from commercially available 2-(2-methyl-3-nitrophenyl)acetic acid, which is converted in five steps into the desired target compound. This procedure offers a convenient alternative route to existing methodologies, given its milder reaction conditions, ease of implementation, and its overall yield (59 %).

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Acknowledgments

This research project was financially supported by the Italian Ministry of Education, University and Research, PRIN grant 2009R7WCZS to MDA. CM wishes to thank the University of Milan for a postdoctoral fellowship.

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Authors and Affiliations

  1. Dipartimento di Scienze Farmaceutiche (Sezione di Chimica Farmaceutica “P. Pratesi”), Università degli Studi di Milano, Via Luigi Mangiagalli, 25, 20133, Milan, Italy

    Carlo Matera, Marta Quadri, Silvia Pelucchi, Marco De Amici & Clelia Dallanoce

Authors
  1. Carlo Matera
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  2. Marta Quadri
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  3. Silvia Pelucchi
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  4. Marco De Amici
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  5. Clelia Dallanoce
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Corresponding author

Correspondence to Carlo Matera.

Additional information

M. Quadri and S. Pelucchi contributed equally to this work.

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Matera, C., Quadri, M., Pelucchi, S. et al. A convenient synthesis of 4-(2-hydroxyethyl)indolin-2-one, a useful intermediate for the preparation of both dopamine receptor agonists and protein kinase inhibitors. Monatsh Chem 145, 1139–1144 (2014). https://doi.org/10.1007/s00706-014-1211-z

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  • DOI: https://doi.org/10.1007/s00706-014-1211-z

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