Solubilizing agents. V. Pyridinecarboxamides was written by Samejima, Masayoshi. And the article was included in Yakugaku Zasshi in 1960.Synthetic Route of C11H15NO2 This article mentions the following:
2-HO2CC5H4N.HCl (120 g.) in 313 g. MeOH and 150 g. concentrated H2SO4 refluxed 5 hrs., the MeOH removed, the residue neutralized with Na2CO3, and the product extracted with C6H6 gave 117 g. 2-MeO2CC5H4N, b11 109-11°. Li (20.9 g.) in 1200 ml. Et2O treated dropwise with 58 ml. PhBr, 139.7 g. 2-MeC5H4N added dropwise, the mixture refluxed 30 min., the product poured onto 1000 g. solid CO2, the Et2O removed, the residue in 1200 ml. EtOH at 0° saturated with dry HCl gas, the EtOH removed, the residue in 750 ml. CHCl3, 338 g. K2CO3, and 188 g. H2O heated, and the CHCl3 layer distilled gave 83.1 g. 2-EtO2CCH2C5H4N, b6 109-12°. 3-HO2CC5H4N (61.8 g.) and 47.1 g. PhOH heated at 110-20°, the mixture treated dropwise with 76.7 g. POCl3, heated at 130-40° until evolution of HCl gas ceased, the product poured into ice H2O, neutralized with Na2CO3, and extracted with C6H6 gave 67.5 g. 3-PhO2CC5H4N, m. 71-2° (EtOH-petr. ether). The above esters and 4-MeO2CC5H4N treated with NH4OH or amines and the products distilled gave x-RHNOCC5H4N (I) (x, R, % yield, and b.p./mm. or m.p. given): 2, H, 90, 105-6°; 2, Me, 77, 118-20°/4; 2, Et, 90, 128-9°/4; 2, Bu, 86, 122-3°/2; 2, HOC2H4, 69, 190-1°/4; 3, Me, 71, 104-5°; 3, Et, 89, 146-7°/3; 3, Bu, 85, 173-4°/3.5; 3, HOC2H4, 71, 90-1° 4, H, 86, 133-4°; 4, Me, 73, 113-14°; 4, Et, 69, 65-6°; 4, Bu, 84, 155-6°/1; 4, HOC2H4, 70, 133-4°. 2-RNHOCH2CC5H4N (II) (R, % yield, b.p./mm. or m.p. given): H, 77, 118-20°; Me, 78, 137°/1; Et, 67, 61-2°; HOC2H4, 67, 94-5°. 3-PhO2CC5H4N (10 g.) and 5 g. PhNH2 (or 2-H2NC5H4N) fused 3 hrs. at 200-10°, the PhOH removed in vacuo, and the product extracted with Et2O gave 3-RNHOCC5H4N (III) (R, % yield, and m.p. given): Ph, 67, 122-3°; 2-pyridyl, 79, 139-41°. Solubilization effects of I, II, and III were studied by use of adrenochrome monosemicarbazone (IV), o-HOC6H4CONH2 (V), p-MeC6H4NH2 (VI), and caffeine (VII). There was practically no difference by the position in isomers of I. II showed increased solubilization activity, the effect being better in lower homologs with Me and Et groups. III was found to give a far stronger effect, while introduction of two alkyls into the N in the acid amide group resulted in increased solubility in the case of V and VI, but 30-40% decrease in the case of IV and VII. II showed a lowering of solubilization activity by 10-40% compared to 3-H2NOCC5H4N. In the experiment, the researchers used many compounds, for example, N,N-Diethylsalicylamide (cas: 19311-91-2Synthetic Route of C11H15NO2).
N,N-Diethylsalicylamide (cas: 19311-91-2) belongs to amides. The amide group is called a peptide bond when it is part of the main chain of a protein, and an isopeptide bond when it occurs in a side chain, such as in the amino acids asparagine and glutamine. 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.Synthetic Route of C11H15NO2
Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics