N-(β-Picolyl)glycine, N-(β-picolyl)-β-aminopropionic acid, and methyl derivatives was written by Wingfield, Harvey N. Jr.. And the article was included in Journal of Organic Chemistry in 1960.Safety of N,N-Diethylsalicylamide This article mentions the following:
The title compounds, 2-C5H4NCH2NHCH2CO2H (I), and 2-C5H4NCH2NH(CH2)2CO2H (II) and the corresponding N-Me derivatives, 2-C5H4NNMeCH2CO2H (III) and 2-C5H4NCH2NMe(CH2)2CO2H (IV), were synthesized for comparison with the metabolic products of nicotine found in dog urine after administration of the alkaloid. H2NCH2CO2Et. HCl (0.1 mole) in a min. of H2O treated with 0.1 mole NaHCO3, the mixture diluted with alc., the filtered solution treated with 0.1 mole 2-C5H4NCHO, the mixture hydrogenated with 100 mg. Pd-C (Raney Ni gave better results), the filtered solution evaporated in vacuo, the residue washed with H2O, taken up in Me2CO, filtered, the solution evaporated, the residue taken up in CHCl3, the filtered solution evaporated, the oily yellow ester (V) (50-60%) from several batches refluxed 48 hrs. with 15% H2SO4, the hydrolyzate boiled with activated C, filtered, the acid solution made alk. with BaCO3, the filtered solution saturated with CO2, the boiled solution filtered, treated with a trace of CaSO4, excess Cd precipitated with H2S, the filtered solution evaporated in vacuo, the acid residue taken up in a min. of H2O, and repeatedly precipitated from H2O with alc.-Me2CO gave I, m. 209-10° (decomposition); thiohydantoin derivative m. 176-7° (decomposition), prepared from azobenzene isothiocyanate according to Ramachandran and McConnell (CA 50, 13879h). V (0.2 mole) and 100 ml. HCHO hydrogenated 3 hrs. with 70-5 mg. Raney Ni at 45 lb./sq. in. gage, the filtered solution concentrated in vacuo, the residue refluxed several days with 15% H2SO4, and the decolorized (C) hydrolyzate worked up as for I yielded quant. III, m. 175-6°; chloroplatinate m. 217° (decomposition) (alc.-H2O). H2C:CHCN (0.47 mole) added dropwise at 0° to 0.5 mole 2-C5H4NNH2, the mixture kept several days at 20° with occasional shaking, fractionated, and the fraction (30%, b. 165-70°) refluxed 20 hrs. with 15% H2SO4 gave on working up 10-12% amorphous II, m. 270° (decomposition); chloroplatinate m. above 250° (decomposition) (alc.-H2O); thioureide m. 174-6° (decomposition). H2C:CHCN (0.4 mole) added slowly with stirring to 0.2 mole 2-C5H4NCH2NH2 containing 4-5 pellets KOH, the mixture kept 2 days at 20°, refluxed several days on a steam bath, filtered, the C6H6 evaporated, and the residue distilled in vacuo gave 2-C5H4NCH2NMeCH2CH2CN, b1.0 121-5°; chloroplatinate m. 228° (decomposition) (alc.-H2O). The nitrile refluxed with 50% H2SO4, the acid hydrolyzate neutralized with Ba(OH)2, the filtered solution saturated with CO2, and the Ba-free product recovered from CHCl3 gave viscous IV, remaining liquid after 6 months in a vacuum desiccator; di-HCl salt m. 205-6° (decomposition); chloroplatinate (alc.-H2O) decomposed without melting. No previous reference to I, II, III, IV was known. 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. In primary and secondary amides, the presence of N–H dipoles allows amides to function as H-bond donors as well. Thus amides can participate in hydrogen bonding with water and other protic solvents; the oxygen atom can accept hydrogen bonds from water and the N–H hydrogen atoms can donate H-bonds. Amides can be freed from solvent or water by drying below their melting points. These purifications can also be used for sulfonamides and acid hydrazides.Safety of N,N-Diethylsalicylamide
Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics