An Easy Access to 7-Methyl-2-naphthalenecarbonitrile

A practical and cost-effective procedure has been developed for the synthesis of 7-methyl-2-naphthalenecarbonitrile, the precursor of the anticoagulant agents YM-60828 or YM-96765. This new route generates the key intermediate in only two steps from readily available 3-cyanopropionaldehyde dimethyl...

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Veröffentlicht in:	Chemical & Pharmaceutical Bulletin 2005, Vol.53(4), pp.448-450
Hauptverfasser:	Koshio, Hiroyuki, Ishihara, Tsukasa, Yamada, Hiroyoshi, Hirayama, Fukushi, Matsumoto, Yuzo, Yanagisawa, Isao
Format:	Artikel
Sprache:	eng
Schlagworte:	Anticoagulants - chemical synthesis Benzaldehydes bicyclic compound Chromatography, Thin Layer condensation cyclization Heterocyclic Compounds - chemical synthesis inhibitor Magnetic Resonance Spectroscopy Naphthalenes - chemical synthesis nitrile Nitriles - chemical synthesis Piperidines - chemical synthesis Spectrophotometry, Ultraviolet
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Beschreibung
Zusammenfassung:	A practical and cost-effective procedure has been developed for the synthesis of 7-methyl-2-naphthalenecarbonitrile, the precursor of the anticoagulant agents YM-60828 or YM-96765. This new route generates the key intermediate in only two steps from readily available 3-cyanopropionaldehyde dimethyl acetal and m-tolualdehyde, without requiring chromatographic purification. The synthesis involves condensation of the cyano derivative with the aldehyde and subsequent cyclodehydration.
ISSN:	0009-2363 1347-5223
DOI:	10.1248/cpb.53.448