Chemical & Pharmaceutical Bulletin 2005-04-01

An easy access to 7-methyl-2-naphthalenecarbonitrile.

Hiroyuki Koshio, Tsukasa Ishihara, Hiroyoshi Yamada, Fukushi Hirayama, Yuzo Matsumoto, Isao Yanagisawa

Index: Chem. Pharm. Bull. 53(4) , 448-50, (2005)

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Abstract

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.