Ethylenediamine → 2,6-Diamino-N2-(2-aminoethyl)-5-nitropyridine

Participants

Reaction Steps

The starting material (2-aminoethyl)(6-amino-5-nitro(2-pyridyl))amine is prepared in the following manner. A mixture of 2-amino-6-chloro-3-nitropyridine (65 g, 376 mmol), acetonitrile (400 ml), and ethylene diamine (500 ml) are stirred overnight (ca. 20 h) at 75–80° C. under argon. When the diamine is added, this reaction can become exothermic! The ethylene diamine is removed under reduced pressure, and then in vacuo (12 h). The completely dried material is suspended in 2M sodium hydroxide solution (500 ml) with vigorous stirring for 30 min. The solid is filtered. The yellow solid is suspended in water (500 ml) with vigorous stirring for 30 min., after which the solid is filtered. The water wash and filtration is repeated one more time to get rid of salts. The yellow solid is dried in vacuo. The crude yellow solid is triturated with ether (3×500 ml) and dried overnight in vacuo resulting in 59 g of 2-(2-aminoethyl)amino-6-amino-5-nitropyridine in >99% purity.

Provenance & Evidence