Brodrick, C. I. et al. published their research in Journal of the Chemical Society in 1951 | CAS: 52250-50-7

Amidines. XVI. A new synthesis of 1-alkyl- and 1-aryl-3, 4-dihydroisoquinolines was written by Brodrick, C. I.;Short, W. F.. And the article was included in Journal of the Chemical Society in 1951.COA of Formula: C15H13N This article mentions the following:

PhCN (10.3 g.) and 12.1 g. PhCH₂CH₂NH₂ (I), treated with 13.4 g. AlCl₃ (20-30 s.) (temperature rise to 220°), heated 30 min. at 165-75°, cooled to 130°, poured into 500 cc. H₂O, the unchanged PhCN (0.2 g.) extracted with ether, the solution made alk. (pH 11), and extracted with C₆H₆, give 55% N-(2-phenylethyl)benzamidinium chloride (II), m. 182-3°; picrate (IIA), lemon yellow, m. 173-4°; the mother liquors yield N, N’-bis(2-phenylethyl)benzamidinium picrate (III), yellow, m. 170-1°; a poor quality of AlCl₃ gave 3.5% III, 74% unchanged PhCN, and 60% I. The low yield of II (47% by the Pinner method) may have been the result of the presence of moisture. PhCH₂CN (23.4 g.), 24.2 g. I, and 26.8 g. AlCl₃ (240°) give 28% of the α-Ph derivative (IV), of III, m. 173.5-4.5°; picrate, m. 113-14°; if the melt is heated 45 min. at 185°, the yield of IV is 21% and 13% PhCH₂CN is recovered. p-NCC₆H₄SO₂Me (18.1 g.), 12.1 g. I, and 13.4 g. AlCl₃(190°) give 2.6% unchanged cyanide and 55% of the p-methylsulfonyl derivative (V) of III, m. 264-5°; picrate, m. 168-8.5°. p-MeOC₆H₄CN (13.3 g.), 12.1 g. I, and 13.4 g. AlCl₃ (140°) give 22% unchanged cyanide, and 52.5% of the p-methoxyphenyl analog (VI) of I, m. 223-3.5°; 3, 4-dimethoxyphenyl analog of I, m. 200.5-1.5° (13%); picrate, orange yellow, m. 165-6°. 3-Cyanopyridine (10.4 g.), 12.1 g. I, and 13.4 g. AlCl₃ (210°) yield 36% (crude) N-2-phenylethylnicotineamidine, m. 131-1.5°; dipicrate, m. 174-5°. AmCN (8 g.), 10 g. I, and 11 g. AlCl₃ (170°) give N-2-phenylethylhexanamidine, as the benzenesulfonate, m. 74-5°. II (7.8 g.) in 81 cc. PhNO₂ and 27 cc. POCl₃, refluxed 2.5 h., gives 43% 3, 4-dihydro-1-phenylisoquinoline, b_1.2 145-54°; V yields 9.7% of the 1-(p-methylsulfonylphenyl) analog as the picrate, yellow, m. 192-2.5°; HCl salt, m. 267-8°. VI gives 3,4-dihydro-1-(p-methoxyphenyl)isoquinoline-HCl, with 1 mol. MeOH, m. 199-200°; it also seps. with 2 mols. H₂O, anhydrous, m. 212-14°; picrate, m. 161.5°. 3,4-Dihydro-1-(3-pyridyl)isoquinoline, b_0.5 155°; dipicrate, m. 196-7°; 1-amyl-3,4-dihydroisoquinoline picrate, m. 112.5-13°. In the experiment, the researchers used many compounds, for example, 1-Phenyl-3,4-dihydroisoquinoline (cas: 52250-50-7COA of Formula: C15H13N).

1-Phenyl-3,4-dihydroisoquinoline (cas: 52250-50-7) belongs to isoquinoline derivatives. The isoquinoline structure occurs in a considerable number of alkaloids in widely separated plant families. It protonates to form salts upon treatment with strong acids, such as HCl. It forms adducts with Lewis acids, such as BF3.COA of Formula: C15H13N

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem