Process for preparing substituted 2-cyanopyridines

Details Process for preparing substituted 2-cyanopyridines Process for preparing substituted 2-cyanopyridines

C - Chemistry, Metallurgy

07

D

C07D 213/84 (2006.01) C07D 215/48 (2006.01) C07D 217/26 (2006.01) C07D 221/04 (2006.01)

Patent

CA 2087315

HOE 92/F 002 Abstract of the disclosure Process for preparing substituted 2-cyanopyridines Compounds of the formula I Image in which R1 is H, alkyl, alkenyl, alkynyl, haloalkyl, alkoxy- carbonyl, alkoxyalkyl, phenyl, benzyl or phenoxy- alkyl, it being possible for the three latter radicals to be substituted in the phenyl moiety; R2 is H, alkyl, alkenyl, alkynyl, haloalkyl or alkoxy- carbonyl; R3 is H, alkyl, alkenyl, alkynyl, haloalkyl, alkoxy- carbonyl, phenyl, phenoxy, benzyl, it being possible for the three latter radicals to be substituted, or alkoxy; and R4 is H, alkyl, alkenyl, alkynyl, haloalkyl or alkoxy- carbonyl; or R1 together with R2 is a saturated chain, and the remaining radicals are as defined above; or R1 together with R2 is a chain of the formula -CH=CH-CH=CH-, which may be substituted, and the remaining radicals are as defined above; HOE 92/F 002 or R3 together with R4 is a chain of the formula -CH=CH-CH=CH-, which may be substituted, and the remaining radicals are as defined above; are valuable intermediates in the preparation of phamaceuticals and crop protection agents. The process according to the invention yields compounds of the formula I by reacting a substituted 1- alkoxypyridinium salt of the formula II, Image in which R1 to R4 have the same meaning as in formula I and R5 is alkyl, alkenyl, alkynyl, benzyl or trialkylsilyl and X is a leaving group; together with a cyanide of the formula III M(CN)m (III), in which M is alkali metal, alkaline earth metal or copper and m is 1 or 2, in a polar, aprotic solvent or mixture of solvents.

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