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

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

1982-04-08

1983-09-20

Bond, Robert T.

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C07D21374

Patent

active

044057903

ABSTRACT:
An improved process for preparing the 2-alkylamino-5-alkylpyridine 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.degree.-120.degree. C. The substituted amination preferably proceeds at a temperature of about 100.degree.-140.degree. 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.

REFERENCES:
Chemical Abstracts, vol. 9, pp. 1919-1920 (1915) abstracting Chichibabin and Seide "J. Russ. Phys. Chem. Soc.", vol. 49, pp. 1216-1236 (1914).
Abramovitch, "Advances in Heterocyclic Chemistry", vol. 6, pp. 274-300 (1966).

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