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