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 acetal and m-tolualdehyde, without requiring chromatographic purification. The synthesis involves condensation of the cyano derivative with the aldehyde and subsequent cyclodehydration.
Koshio
Hiroyuki
H
Institute for Drug Discovery Research, Yamanouchi Pharmaceutical Co. Ltd., Ibaraki. koshio@yamanouchi.co.jp
Ishihara
Tsukasa
T
Yamada
Hiroyoshi
H
Hirayama
Fukushi
F
Matsumoto
Yuzo
Y
Yanagisawa
Isao
I
D000925:Anticoagulants / Q000138:chemical synthesis*; D001547:Benzaldehydes; D002855:Chromatography, Thin Layer; D006571:Heterocyclic Compounds / Q000138:chemical synthesis; D009682:Magnetic Resonance Spectroscopy; D009281:Naphthalenes / Q000138:chemical synthesis*; D009570:Nitriles / Q000138:chemical synthesis*; D010880:Piperidines / Q000138:chemical synthesis; D013056:Spectrophotometry, Ultraviolet
C502177:7-methyl-2-naphthalenecarbonitrile; D000925:Anticoagulants; D001547:Benzaldehydes; D006571:Heterocyclic Compounds; D009281:Naphthalenes; D009570:Nitriles; D010880:Piperidines; C111032:YM 60828; C502178:YM-96765