The action of mixed organomagnesium compounds on several aromatic amides with hydroxyl or alkoxyl groups was written by Couturier, Paul. And the article was included in Compt. rend. in 1937.Formula: C11H15NO2 This article mentions the following:
Under conditions in which EtMgBr reacts with o-HOC6H4CONEt2 to give 85% ketone and with the p-isomer to give 5%, it reacts with the corresponding 2,4-di-OH compound to give 10% 2,4-dihydroxypropiophenone. The diethylamides of o- and p-MeOC6H4CO2H (I), 3,4-dihydroxy- and 3,4,5-trihydroxybenzoic acid (II) give with EtMgBr 60-80% of mono-, di- or trimethoxypropiophenones. The diethylamide of anisic acid gives the corresponding ketone and also Et2NCPh2C6H4OMe which is decomposed by acids to Et2NH and HOCPh2C6H4OMe. Simple amides of I and II with EtMgBr give 70% of the same ketones, mixed with the corresponding imides, which m. 45° and 48°, resp. In the experiment, the researchers used many compounds, for example, N,N-Diethylsalicylamide (cas: 19311-91-2Formula: C11H15NO2).
N,N-Diethylsalicylamide (cas: 19311-91-2) belongs to amides. Amides include many other important biological compounds, as well as many drugs like paracetamol, penicillin and LSD. Low-molecular-weight amides, such as dimethylformamide, are common solvents. Amides can be recrystallised from large quantities of water, ethanol, ethanol/ether, aqueous ethanol, chloroform/toluene, chloroform or acetic acid. The likely impurities are the parent acids or the alkyl esters from which they have been made. The former can be removed by thorough washing with aqueous ammonia followed by recrystallisation, whereas elimination of the latter is by trituration or recrystallisation from an organic solvent.Formula: C11H15NO2
Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics