Facile acidic hydrolysis and displacement reactions of 2‐chloro‐and 2,9‐dichloro‐1,10‐phenanthroline
Authors:
- 1 July 2008
- journal article
- research article
- Published by Wiley in Journal of Heterocyclic Chemistry
- Vol. 45 (4) , 1167-1170
Abstract
Magnified image Treatment of 2‐chloro‐ or 2,9‐dichloro‐1,10‐phenanthroline with aqueous HBr or aqueous H2SO4 at 120°C yielded 1,10‐phenanthroline‐2(1H)‐one or 1,10‐dihydro‐1,10‐phenanthroline‐2,9‐dione, respectively. The hydrolysis of 2,9‐dichloro‐1,10‐phenanthroline with 37% aqueous HC1 led to the half hydrolyzed amide and the bis‐amide. Under comparable reactions conditions, using aqueous HBr, H2SO4 or HC1, 2‐chloropyridine was found to be hydrolytically stable. On the other hand, 2‐chloro‐ or 2,9‐dichloro‐1,10‐phenanthroline on heating with 57% aqueous HI afforded the HI salts of 2‐iodo‐ or 2,9‐diiodo‐1,10‐phenanthroline, which could be isolated. These salts on treatment with aqueous ammonium hydroxide led to good yields of 2‐iodo‐ and 2, 9‐diiodo‐1,10‐phenanthroline, respectively. Treatment of 2‐chloropyridine with 57% aqueous HI under similar reaction conditions led to 2‐iodopyridine in a 10% conversion.Keywords
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