3-(Aminomethyl)pyridine

CLEAR COLOURLESS TO SLIGHLY YELLOW LIQUID

It finds its application as a rubefacient.

3-(Aminomethyl)pyridine can be used to prepare metal complexes. A number of complexes of cobalt(II), nickel(II) and copper(II) thiocyanates, chlorides and bromides with 3-pyridine amine were prepared and the stereochemical configurations of these complexes were deduced using spectroscopy and magnetism, and the decomposition of the complexes was studied by thermogravimetry and differential thermal analysis^[2].

Synthesis of 3-(aminomethyl)pyridine by traceless C3-selective umpolung of 1-amidopyridin-1-ium salts. A natural product inspired rapid access of 3-(aminomethyl)pyridine by one-pot reaction of 1-amidopyridin-1-ium salt with aminal followed by reductive cleavage of the N–N bond is developed. This C3-selective formal C–H activation of pyridine features a traceless umpolung of the 1-amidopyridin-1-ium salt toward a Mannich type C–C bond formation of the in situ generated 1-amido-2-dialkylamino-1,2-dihydropyridine intermediate^[1].

[1] TANG P, XIAO D, WANG B. Synthesis of 3-(aminomethyl)pyridine by traceless C3-selective umpolung of 1-amidopyridin-1-ium salts[J]. Chemical Communications, 2017. DOI:10.1039/C6CC09582H.
[2] J. R. ALLAN  M. J P  A D Paton. The preparation, characterisation and thermal analysis studies on complexes of cobalt(II), nickel(II), and copper(II) with 3-picolylamine[J]. Journal of Thermal Analysis and Calorimetry, 1985. DOI:10.1007/BF01913603.