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synthetic communication.pdf
SYNTHETIC COMMUNICATIONSw
Vol. 34, No. 6, pp. 1097–1103, 2004
Facile and Selective Synthesis of
Chloromethylpyridines and
Chloropyridines Using
Diphosgene/Triphosgene#
P. Narendar, B. Gangadasu, Ch. Ramesh, B. China Raju,
and V. Jayathirtha Rao*
Organic Chemistry Division II, Indian Institute of Chemical Technology,
Hyderabad, India
ABSTRACT
Diphosgene and triphosgene in the presence of amines were found to be
an excellent chlorinating agents with high selectivity for the preparation
of chloromethylpyridines and chloropyridines from picoline-N-oxides
and pyridine-N-oxides respectively.
Key Words: Chloromethyl pyridine; Chloropyridine; Diphosgene;
Triphosgene.
#IICT Communication No: 030808.
*Correspondence: V. Jayathirtha Rao, Organic Chemistry Division II, Indian Institute
of Chemical Technology, Hyderabad-500007, India; E-mail: jrao@iict.res.in.
1097
DOI: 10.1081/SCC-120028642 0039-7911 (Print); 1532-2432 (Online)
Copyright # 2004 by Marcel Dekker, Inc.
ORDER REPRINTS
1098 Narendar et al.
Chloromethylpyridines and chloropyridines constitute an important class
of compounds in the preparation of pharmaceuticals, dyes,[1] and pesticides.[2]
The most common method for the preparation of chloromethylpyridines and
chloropyridines involve the chlorination of picolines[3] and pyridine-N-
oxides[4] with reagents such as POCl ,[5] SO Cl ,[6] phosgene in DMF,[7]
3 2 2
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