The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《2-(4-Pyridyl)benzimidazole-3-carboxylic acid》. Authors are Leko, A. M.; Bastic, B. L..The article about the compound:2-(Pyridin-4-yl)-1H-benzo[d]imidazolecas:2208-59-5,SMILESS:C1(C2=CC=NC=C2)=NC3=CC=CC=C3N1).HPLC of Formula: 2208-59-5. Through the article, more information about this compound (cas:2208-59-5) is conveyed.
cf. C.A. 46, 8655. A mixture of cinchomeronic acid (5.4) and ο-C6H4(NH2)2 (3.3 g.) is heated in a paraffin bath to 200° (20 min.), cooled, and dissolved in Ac2O. After some time a yellow precipitate is formed, which is purified by dissolving in C6H6 and precipitating with light petroleum. It consists of the lactam of 2-(4-pyridyl)benzimidazole-3-carboxylic acid (45%), C13H7ON3, m. 208-9°, which is warmed with 10 mL. of H2O and 1 mL. of 0.25N KOH until the yellow color disappears. Dilute HCl is then added and 2-(4-pyridyl) benzimidazole-3-carboxylic acid (50%), C13H9O2N3, m. 258-9° is precipitated The acid heated in a paraffin bath to 280° gives 2-(4-pyridyl)benzimidazole, m. 214°.
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Reference:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles