Well-Defined Phosphine-Free Iron-Catalyzed N-Ethylation and N-Methylation of Amines with Ethanol and Methanol was written by Lator, Alexis;Gaillard, Sylvain;Poater, Albert;Renaud, Jean-Luc. And the article was included in Organic Letters in 2018.Product Details of 4714-63-0 This article mentions the following:
An iron(0) complex bearing a cyclopentadienone ligand catalyzed N-methylation and N-ethylation of aryl and aliphatic amines with methanol or ethanol in mild and basic conditions through a hydrogen autotransfer borrowing process is reported. A broad range of aromatic and aliphatic amines underwent mono- or dimethylation in high yields. DFT calculations suggest mol. hydrogen acts not only as a reducing agent but also as an additive to displace thermodn. equilibrium In the experiment, the researchers used many compounds, for example, 4-(Ethylamino)benzonitrile (cas: 4714-63-0Product Details of 4714-63-0).
4-(Ethylamino)benzonitrile (cas: 4714-63-0) belongs to nitriles. The R-C-N bond angle in and nitrile is 180° which give a nitrile functional group a linear shape. Both the carbon and the nitrogen are sp hydridized which leaves them both with two p orbitals which overlap to form the two π bond in the triple bond. Industrially, the main methods for producing nitriles are ammoxidation and hydrocyanation. Both routes are green in the sense that they do not generate stoichiometric amounts of salts.Product Details of 4714-63-0
Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts