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Monatshefte für Chemie - Chemical Monthly

, Volume 145, Issue 7, pp 1139–1144 | Cite as

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

  • Carlo Matera
  • Marta Quadri
  • Silvia Pelucchi
  • Marco De Amici
  • Clelia Dallanoce
Original Paper

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 %).

Graphical Abstract

Keywords

D2/D3 agonists Heterocycles Indolin-2-ones One-pot synthesis Ropinirole Synthetic improvement 

Notes

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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Copyright information

© Springer-Verlag Wien 2014

Authors and Affiliations

  • Carlo Matera
    • 1
  • Marta Quadri
    • 1
  • Silvia Pelucchi
    • 1
  • Marco De Amici
    • 1
  • Clelia Dallanoce
    • 1
  1. 1.Dipartimento di Scienze Farmaceutiche (Sezione di Chimica Farmaceutica “P. Pratesi”)Università degli Studi di MilanoMilanItaly

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