Compound(3724-19-4)Quality Control of 3-Pyridinepropionic acid received a lot of attention, and I have introduced some compounds in other articles, similar to this compound(3-Pyridinepropionic acid), if you are interested, you can check out my other related articles.
The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Isoquinolines. III. The nitration of 3,4-dihydro- and 1,2,3,4-tetrahydroisoquinolines》. Authors are McCoubrey, A.; Mathieson, DavidW..The article about the compound:3-Pyridinepropionic acidcas:3724-19-4,SMILESS:OC(=O)CCC1=CC=CN=C1).Quality Control of 3-Pyridinepropionic acid. Through the article, more information about this compound (cas:3724-19-4) is conveyed.
cf. C.A. 45, 1137i. 3,4-Dihydroisoquinoline(600 mg.) in 2.5 cc. H2SO4 (d. 1.84), added to 500 mg. KNO3 in 2.5 cc. H2SO4 at 0° and the mixture allowed to warm to room temperature (2 hrs.) and warmed 4 hrs. at 60° gives 700 mg. of a brown compound (presumably the 7-NO2 derivative), m. 88-90°; dehydrogenation by refluxing 2 hrs. with 200 mg. Pd black in 10 cc. tetrahydronaphthalene gives 170 mg. 7-nitroisoquinoline, m. 177-8°. Tetrahydroisoquinoline (10.5g.) converted into the sulfate by solution in the calculated amount of 5 N H2SO4, evaporated to dryness, the residue added to 10 g. KNO3 in 50 cc. concentrated H2SO4 at 0° kept overnight at room temperature, poured on ice, the mixture neutralized with aqueous NH3, the base extracted with CHCl3, the CHCl3 evaporated, and the residue extracted with petr. ether, gives the unstable 1,2,3,4-tetrahydro-7-nitroisoquinoline, analyzed as the HCl salt (I), in. 261° (12.5 g.); picrate, brown, m. 190-2°; 2-(p-nitro-benzoyl) derivative, yellow, m. 209-10°; 2-Bz derivative (IA), yellow, in. 125° I (5 g.) in 150 cc. EtOH, reduced over 300 mg. Pt oxide, gives 2.35 g. 7-amino-1,2,3,4-tetrahydroisoquinoline, m. 120-1°. IA (4.3 g.) in 100 cc. EtOH, reduced over Raney Ni (3 hrs.), gives 3.8 g. 7-amino-2-benzoyl-1,2,3,4-tetrahydroisoquinoline (II), cream, m. 129°; 1 g. II and 500mg. LiAlH4 in 100 cc. ether, refluxed overnight, give 900 mg. 2-benzyl analog (III), cream, m. 88°. 5,2-O2N(ClCH2CH2)C6H3CH2Cl (2.5 g.) and 3.5 g. PhCH2NH2 in 25 cc. EtOH, refluxed 1 hr., give 3 g. 2-benzyl-7-nitro-1,2,3,4-tetrahydro-isoquinoline-HCl (IV), m. about 248°; reduction of 1 g. IV over Raney Ni (10 hrs.) gives 500 mg. III. Isoquinoline (5 g.) and 5 g. PhCH2Cl in 10 cc. EtOH, refluxed 6 hrs. and the product in H2O treated with excess KI, give 14 g. 2-benzylisoquinolinium iodide (V), yellow, in. 178°; 10 g. V in 100 cc. MeOH, reduced (6 hrs.) over 300 mg. Pt oxide, gives 6.2 g. 2-benzyl-1,2,3,4-tetrahydroisoquinoline, b20 200-5°; HCl salt, m. 204°; nitration gives IV. 2-Butyl-1,2,3,4-tetrahydroisoquinoline and KNO3 in concentrated H2SO4 give the 7-NO2 derivative (HCl salt, m. 234-5°).
Compound(3724-19-4)Quality Control of 3-Pyridinepropionic acid received a lot of attention, and I have introduced some compounds in other articles, similar to this compound(3-Pyridinepropionic acid), if you are interested, you can check out my other related articles.
Reference:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem