The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Ionic liquid catalysed aerobic oxidative amidation and thioamidation of benzylic amines under neat conditions》. Authors are Joshi, Abhisek; Kumar, Rahul; Semwal, Rashmi; Rawat, Deepa; Adimurthy, Subbarayappa.The article about the compound:Picolinamidecas:1452-77-3,SMILESS:O=C(N)C1=NC=CC=C1).Safety of Picolinamide. Through the article, more information about this compound (cas:1452-77-3) is conveyed.
Tetrabutylammonium hydroxide (TBAOH) was discovered as a highly efficient and green catalyst for aerobic oxidation of the α-methylene carbon of primary amines as well as benzylic groups RCH2NH2 (R = Ph, pyren-1-yl, thiophene-2-yl, etc.) into the corresponding amides RC(O)NH2 and ketones R1C(O)C6H5 [R1 = Ph, pyridin-2-yl, C6H5C(O)] and 9H-fluoren-9-one under neat conditions. Ionic liquid TBAOH catalyzed aerobic oxidation of benzyl amines to benzamides and with elemental sulfur was described; and the corresponding benzylbenzothioamides RC(S)NHCH2R were obtained under metal-free, oxidant-free and base-free conditions. Applicability at the gram scale for the synthesis of the desired amides/ketones is also demonstrated with the present protocol.
After consulting a lot of data, we found that this compound(1452-77-3)Safety of Picolinamide can be used in many types of reactions. And in most cases, this compound has more advantages.
Reference:
Tetrahydroisoquinoline – Wikipedia,
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem