Chemistry:2-Chloromethylpyridine
2-Chloromethylpyridine is an organohalide that consists of a pyridine core bearing a chloromethyl group. It is one of three isomeric chloromethylpyridines, along with 3- and 4-chloromethylpyridine. It is an alkylating agent.
Preparation and reactions
It can be prepared by reaction of 2-methylpyridine with chlorine. A more efficient route involves treating 2-picoline-N-oxide with phosphoryl chloride in the presence of triethylamine:[1]
- CH
3C
5H
4NO + POCl
3 + Et
3N → ClCH
2C
5H
4N + Et
3NH+
[PO
2Cl
2]−
(Et = C2H5)
A related method uses triphosgene in place of phosphoryl chloride.[2]
2-Chloromethylpyridine is a precursor to pyridine-containing ligands.[3][4]
Safety
2-Chloromethylpyridine is an analogue of nitrogen mustards, and has been investigated for its mutagenicity.[citation needed]
Applications
2-Picolyl chloride has application in the synthesis of the following drugs:
- AD-35 [1531586-58-9]
- Capravirine
- Pifenate [15686-87-0]
- Pimeprofen [64622-45-3]
- SDZ NDD 094 [148257-48-1]
References
- ↑ Ash, Mary Lynne; Pews, R. Garth (1981). "The Synthesis of 2-Chloromethylpyridine from 2-Picoline-N-Oxide". Journal of Heterocyclic Chemistry 18 (5): 939–940. doi:10.1002/jhet.5570180518.
- ↑ Narendar, P.; Gangadasu, B.; Ramesh, Ch.; China Raju, B.; Jayathirtha Rao, V. (2004). "Facile and Selective Synthesis of Chloromethylpyridines and Chloropyridines Using Diphosgene/Triphosgene". Synthetic Communications 34 (6): 1097–1103. doi:10.1081/SCC-120028642.
- ↑ Buhaibeh, Ruqaya; Duhayon, Carine; Valyaev, Dmitry A.; Sortais, Jean-Baptiste; Canac, Yves (2021). "Cationic PCP and PCN NHC Core Pincer-Type Mn(I) Complexes: From Synthesis to Catalysis". Organometallics 40 (2): 231–241. doi:10.1021/acs.organomet.0c00717. https://hal.archives-ouvertes.fr/hal-03128570.
- ↑ Rapko, B. M.; Duesler, E. N.; Smith, P. H.; Paine, R. T.; Ryan, R. R. (1993). "Chelating Properties of 2-((Diphenylphosphino)methyl)pyridine N,P-dioxide and 2,6-Bis((diphenylphosphino)methyl)pyridine N,P,P'-trioxide Toward f-Element Ions". Inorganic Chemistry 32 (10): 2164–2174. doi:10.1021/ic00062a047.
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