Fisher, Gary B. et al. published their research in Tetrahedron Letters in 1993 | CAS: 19311-91-2

N,N-Diethylsalicylamide (cas: 19311-91-2) belongs to amides. The solubilities of amides and esters are roughly comparable. Typically amides are less soluble than comparable amines and carboxylic acids since these compounds can both donate and accept hydrogen bonds. Tertiary amides, with the important exception of N,N-dimethylformamide, exhibit low solubility in water. Amides are not in general accessible by the direct condensation of amines with carboxylic acids for two reasons: first, both components are readily deactivated by a transfer of a proton from the acid to the amine and second, the hydroxy unit on the carbonyl of the acid is a relatively poor leaving group. Nevertheless, the formation of five- and six-membered rings is often surprisingly simple provided that other factors can be brought into play to assist in the condensation.Formula: C11H15NO2

Aminoborohydrides. 3. A facile reduction of tertiary amides to the corresponding amines and alcohols in high purity using lithium aminoborohydrides. Sterically controlled selective carbon-nitrogen or carbon-oxygen bond cleavage was written by Fisher, Gary B.;Fuller, Joseph C.;Harrison, John;Goralski, Christian T.;Singaram, Bakthan. And the article was included in Tetrahedron Letters in 1993.Formula: C11H15NO2 This article mentions the following:

Lithium aminoborohydrides (LiABH3), obtained by the reaction of n-BuLi with amine-boranes, are powerful reducing agents for the reduction of tertiary amides to the corresponding amines or alcs. Lithium pyrrolidinoborohydride and lithium diisopropylaminoborohydride reduce both aliphatic and aromatic tertiary amides to give either the corresponding alc. or amine, depending on the steric requirement of the tertiary amide and the LiABH3 used. The yields of amines and alcs. from this procedure range from very good to essentially quant. 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. The solubilities of amides and esters are roughly comparable. Typically amides are less soluble than comparable amines and carboxylic acids since these compounds can both donate and accept hydrogen bonds. Tertiary amides, with the important exception of N,N-dimethylformamide, exhibit low solubility in water. Amides are not in general accessible by the direct condensation of amines with carboxylic acids for two reasons: first, both components are readily deactivated by a transfer of a proton from the acid to the amine and second, the hydroxy unit on the carbonyl of the acid is a relatively poor leaving group. Nevertheless, the formation of five- and six-membered rings is often surprisingly simple provided that other factors can be brought into play to assist in the condensation.Formula: C11H15NO2

Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics