Process for preparing 2-alkylamino- and 2-amino-5-...

Details Process for preparing 2-alkylamino- and 2-amino-5-... Process for preparing 2-alkylamino- and 2-amino-5-...

C - Chemistry, Metallurgy

07

D

260/297

C07D 213/74 (2006.01) C07D 213/73 (2006.01)

Patent

CA 1219589

ABSTRACT An improved process for preparing the 2-alkylamino-5-alkyl- pyridine and 2-amino-5-alkylpyridine amination products of 3-alkylpyridines, comprising the step of initially reacting the base directly with the sodium salt of a primary alkylamine to produce the 2-alkylamino form, wherein the alkyl group in each reactant has from 1 to about 20 carbon atoms. The sodium salt is preferably preformed in situ by adding the alkylamine to a dispersion of sodium in an organic solvent heated to about 100-120°C. The substituted amination preferably proceeds at a temperature of about 100-140°C in a solvent such as toluene and under an inert nitrogen atmosphere. The ratio of 2,5-:2,3- isomer products of the reaction is up to about 10:1 or more, with the effective yield of the 2,5-alkylated isomer being about 25% or more. This recovered 2-alkylamino-5-alkylpyridine product is readily dealkylated by reaction with hydrobromic or hydriodic acid with or without the presence of a pyridine hydrohalide salt to obtain the 2-amino-5-alkylpyridine product which has proven uses in herbicidal, insecticidal and pharmaceutical applications.

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