The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《N-Substituted 1,2,3,4-tetrahydroquinolines》. Authors are Rachinskii, F. Yu.; Slavachevskaya, N. M.; Sovalkova, L. K..The article about the compound:2-(3,4-Dihydroquinolin-1(2H)-yl)ethanaminecas:37481-18-8,SMILESS:NCCN1CCCC2=C1C=CC=C2).Formula: C11H16N2. Through the article, more information about this compound (cas:37481-18-8) is conveyed.
Passage of ethylene oxide into 266 g. 1,2,3,4-tetrahydroquinoline and 1 ml. H2O at 25-30° gave 48 g. N-(2-hydroxyethyl)-1,2,3,4-tetrahydroquinoline (I), b5 140-4° n20D 1.5740, d20 1.1041, 68 g. N-[2-(2-hydroxyethoxy)ethyl]analog, b4 167-70°, 1.5523, 1.1055, and 7 g. N-[2-[2-(2-hydroxyethoxy)ethoxy]ethyl]analog, b5 205-7°, 1.5420, 1.1053. I.HBr m. 120-2°. Adding 0.1 mole N-(2-cyanoethyl)1,2,3,4-tetrahydroquinoline (II) in EtOH to 40 g. powd. Ni-Al alloy in 1% NaOH and refluxing 4 hrs. gave after addition of HCl, evaporation, and treatment with NaOH, 63% N-(3-aminopropyl)-1,2,3,4-tetrahydroquinoline, b5 137-40°, 1.5777, 1.0450 (di-HBr salt m. 195-7°). II refluxed with alc. KOH gave 73% N-(2-carboxyethyl)-1,2,3,4-tetrahydroquinoline, m. 70-2°. Tetra-hydroquinoline and BrCH2CH2NH2.HBr treated with EtONa in EtOH and refluxed 2 hrs. gave 7% N-(2-aminoethyl)-1,2,3,4-tetrahydroquinoline, b5 130-2°, 1.5830, 1.0645. Similarly was prepared 10% N-(2-diethylaminoethyl)analog, b5 160-1°, 1.5475, 0.9836. Tetrahydroquinoline and ethylene sulfide in C6H6 in 5 hrs. refluxing gave 6.7% N-(2-mercaptoethyl)-1,2,3,4-tetrahydroquinoline, b5 145°, 1.5990, 1.0903, which treated with a stream of air in EtOH in the presence of FeSO4 gave the corresponding disulfide, isolated as di-HCl salt, m. 118-20°. The mercapto derivative formed an HBr salt, m. 176-7°. Tetrahydroquinoline, CS2, and KOH in C6H6-H2O gave in 2 hrs. 65% K 1,2,3,4-tetrahydroquinolyldithiocarbamate, m. 264-6°. Tetrahydroquinoline and o-C6H4(CO)2O in C6H6 refluxed 3 hrs. gave 57% N,N’-di(1,2,3,4-tetrahydroquinolyl)phthalamide, m. 173-4°. Similarly, o-MeO2CC6H4COCl gave 30% 2-carbomethoxyphthalo-1,2,3,4-tetrahydroquinolide, m. 63-5°, b5 210°. Tetrahydroquinoline and undecylenic acid heated finally at 230° gave 23% N-undecylenyl-1,2,3,4-tetrahydroquinoline, b5 152°, 1.519, 0.9872. Tetrahydroquinoline failed to react with ethylenimine. The products above were tested successfully as antioxidants, insect repellents, and anticorrosion agents.
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Reference:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics