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Facile acidic hydrolysis and displacement reactions of 2‐chloro‐and 2,9‐dichloro‐1,10‐phenanthroline
Author(s) -
Krapcho A. Paul,
Sparapani Silvia
Publication year - 2008
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570450435
Subject(s) - chemistry , phenanthroline , hydrolysis , aqueous solution , ammonium hydroxide , amide , medicinal chemistry , nuclear chemistry , organic chemistry
Treatment of 2‐chloro‐ or 2,9‐dichloro‐1,10‐phenanthroline with aqueous HBr or aqueous H 2 SO 4 at 120°C yielded 1,10‐phenanthroline‐2(1 H )‐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, H 2 SO 4 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.