The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Isoquinoline compounds. IV. Synthesis of 1-[2-(3-pyridyl) ethyl] -6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline》. Authors are Livshits, R. S.; Evstigneeva, R. P.; Bainova, M. S.; Preobrazhenskii, N. A..The article about the compound:3-Pyridinepropionic acidcas:3724-19-4,SMILESS:OC(=O)CCC1=CC=CN=C1).Related Products of 3724-19-4. Through the article, more information about this compound (cas:3724-19-4) is conveyed.
Conventional esterification gave 80% Me nicotinate, b7 89-90°, m. 38°, which with N2H4.H2O gave 98-9% hydrazide, m. 158-9°; this with BzCl at 0° gave 96.5% N-Bz derivative, m. 185-6°, which, heated in (CH2OH)2 with Na2CO3 2 min. to 160° yielded 28-30% nicotinaldehyde, b12 85-90°, condensed with CH2(CO2H)2 to 3-pyridineacrylic acid, m. 232-3° (from EtOH). This (8 g.),40 ml. AcOH, 80 ml. HI (d. 1.71), and 3 g. red P refluxed 14-15 hrs. gave 90% 3-pyridinepropionic acid-HI, m. 163-4°, yielding with Na2HPO4 the free acid, m. 157-8° (from EtOH) [Et ester (75.7% with EtOH-HCl), b7 129-30°, nD20 1.4983, d2020 1.071; HCl salt, m. 95-6°; picrate, m. 81-2°]. The Et ester (3 g.) and 3 g. 3,4-(MeO)2C6H3CH2CH2NH2 heated with a few drops of pyridine 3 hrs. at 180° gave 80.7% N-(3,4-dimethoxyphenethyl)-3-pyridinepropionamide m. 103°, which heated with POCl3 2.5 hrs. at 100° yielded 85% 1-[2-(3-pyridyl)ethyl]-6,7-dimethoxy-3,4-dihydroisoquinoline, m. 88-9° (from petr. ether); HCl salt, m. 198-200° (from EtOH). The free base (1 g.), 30 ml. H2O, 4 g. Zn dust, and 0.1 g. CuSO4 treated with 3 ml. concentrated H2SO4 and gently heated 1 hr., then heated more strongly 2 hrs., gave 70% 1-[2-(3-pyridyl)ethyl]-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline, an oil; HCl salt, m. 241-3° (from EtOH).
In some applications, this compound(3724-19-4)Related Products of 3724-19-4 is unique.If you want to know more details about this compound, you can contact with the author or consult more relevant literature.
Reference:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem