Crystallographic and spectroscopic characterization of 5-chloro-pyridine-2,3-di-amine.

Aron Sulovari,Joseph M Tanski

doi:10.1107/s2056989017010489

Aron Sulovari, Joseph M Tanski

Open Access

https://doi.org/10.1107/s2056989017010489

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Abstract

The two ortho-amino groups of the title compound, C5H6ClN3, twist out of the plane of the mol-ecule to minimize intra-molecular inter-action between the amino hydrogen atoms. In the crystal, the amino groups and the pyridine N atom engage in inter-molecular hydrogen bonding. The mol-ecules pack into spiral hydrogen-bonded columns with offset face-to-face π-stacking.

Highlights

Chemical contextThe title compound, 5-chloropyridine-2,3-diamine, is a trisubstituted pyridine featuring ortho-amino groups and a chlorine atom
The two ortho-amino groups of the title compound, C5H6ClN3, twist out of the plane of the molecule to minimize intramolecular interaction between the amino hydrogen atoms
While all of the sixteen isomers of 5-chloropyridine-2,3-diamine are commercially available, none of their crystal structures have been reported in the literature. 5Chloropyridine-2,3-diamine may be produced by nitrating 2amino-5-chloropyridine with nitric acid to give 2-amino-3nitro-5-chloropyridine, which is reduced with sodium dithionite (Israel & Day, 1959)

Summary

Chemical context

The title compound, 5-chloropyridine-2,3-diamine, is a trisubstituted pyridine featuring ortho-amino groups and a chlorine atom. The reduction may be accomplished with hydrogen gas and Pd/C (Xie et al, 2016). 5Chloropyridine-2,3-diamine has proven useful as a reagent in complex syntheses, such as in the synthesis of aldose reductase inhibitors with antioxidant activity (Han et al, 2016), the regioselective functionalization of imidazopyridines via alkenylation catalyzed by a Pd/Cu catalyst (Baladi et al, 2016), the preparation of amino acid oxidase inhibitors (Xie et al, 2016), the preparation of -glucuronidase inhibitors (Taha et al., 2016), the preparation of imidazopyridine derivatives with activity against MCF-7 breast adenocarcinoma (Püsküllü et al., 2015) and the preparation of dihydroxyarene-substituted benzimidazoles, quinazolines and larger rings via cyclocondensation of diamines (Los et al, 2012)

Structural commentary

Supramolecular features

Database survey

Analytical data

Refinement