Anionic ortho-Fries rearrangement, a facile route to arenol-based Mannich bases was written by Assimomytis, Nikos;Sariyannis, Yiannis;Stavropoulos, Georgios;Tsoungas, Petros G.;Varvounis, George;Cordopatis, Paul. And the article was included in Synlett in 2009.Safety of N,N-Diethylsalicylamide This article mentions the following:
Phenol and 1-naphthol-based carbamates undergo the anionic ortho-Fries rearrangement to their corresponding amides. Bulky substitution at position 8 of 1-naphthol-based carbamates makes the rearrangement an exclusive reaction, even at -90°, under a variety of conditions. The amides can be efficiently reduced to the corresponding Mannich bases. A novel route to 7-[(dialkylamino)methyl]-8-hydroxy-1-naphthaldehydes is presented. In the experiment, the researchers used many compounds, for example, N,N-Diethylsalicylamide (cas: 19311-91-2Safety of N,N-Diethylsalicylamide).
N,N-Diethylsalicylamide (cas: 19311-91-2) belongs to amides. Because of the greater electronegativity of oxygen, the carbonyl (C=O) is a stronger dipole than the N–C dipole. The presence of a C=O dipole and, to a lesser extent a N–C dipole, allows amides to act as H-bond acceptors. Ionic, or saltlike, amides are strongly alkaline compounds ordinarily made by treating ammonia, an amine, or a covalent amide with a reactive metal such as sodium.Safety of N,N-Diethylsalicylamide
Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics