RESEARCH ARTICLE

 

Selective bromination of 4-chloro-1-indanone and synthesis of (4-chloro-2, 3-dihydro-1H-indene-2-yl)methanamine

 

 

S. Jasouri^{I, II}; J. Khalafy^{I, *}; M. Badali^II; M. Piltan^I

^IDepartment of Chemistry, Urmia University, Urmia 57154, Iran
^IIDaana Pharmaceutical Co., P.O. Box 5181-51575, Tabriz, Iran

 

 

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ABSTRACT

The synthesis of 4-chloro-1-indanone in four steps from 2-chlorobenzaldehyde was investigated. Bromination of this compound under various conditions occurred in the cyclopentanone ring, producing mono- and dibromo derivatives. Cyanation of 2-bromo-4-chloro-1-indanone followed by reduction gave (4-chloro-2, 3-dihydro-1H-indene-2-yl)methanamine in quantitative yield.

Keywords: Indanone, bromination, cyanation, reduction, GABA_B receptors

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Acknowledgements

We are grateful for financial support from Urmia University and Daana Pharmaceutical Co. and S.J. is grateful to Daana Pharmaceutical Co. for a Ph.D. scholarship.

 

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Received 23 June 2010
Revised 10 July 2010
Accepted 12 July 2010

 

 

* To whom correspondence should be addressed. E-mail: j.khalafi@mail.urmia.ac.ir ; jkhalafi@yahoo.com