Brodrick, C. I. et al. published their research in Journal of the Chemical Society in 1949 | CAS: 52250-50-7

1-Phenyl-3,4-dihydroisoquinoline (cas: 52250-50-7) belongs to isoquinoline derivatives. Although isoquinoline derivatives can be synthesized by several methods, relatively few direct methods deliver the unsubstituted isoquinoline. They are also used to make oil-soluble dyes, food colorants, pharmaceuticals, pH indicators and other organic compounds. Reference of 52250-50-7

Disproportionation of dihydroisoquinolines was written by Brodrick, C. I.;Short, W. F.. And the article was included in Journal of the Chemical Society in 1949.Reference of 52250-50-7 This article mentions the following:

PhCH2CH2NHBz, cyclized by the method of Pictet and Kay (C.A. 3, 2434), gives 66% 1-phenyl-3,4-dihydroisoquinoline (I), b1.2 146-9.5°. Distillation of 21.8 g. I at 340-5° and redistillation at 1.2-1.4 mm. (148-55°) gives 19.7 g. of a product which, crystallized from petr. ether, yields 14.1 g. of a mixture (II), m. 70-5°, and 3.3 g., m. 73-7°. II with picric acid gives the picrate of 1-phenylisoquinoline (III), m. 167-7.5°; with HCl in ether II yields the HCl salt, m. 227-9°, of 1-phenyl-1,2,3,4-tetrahydroisoquinoline (IV). II (5 g.) in 7 cc. CHCl3 and 125 cc. petr. ether gives 1.03 g. IV. Adsorption of 1 g. of II in 150 cc. petr. ether on activated Al2O3 and elution with petr. ether give 0.28 g. III and 0.2 g. IV. II (5 g.) and 37.5 cc. Ac2O, heated 3 hrs. at 100° and the product separated into basic and neutral fractions with HCl in ether, give 2.46 g. III and 2.5 g. of the 2-Ac derivative of IV, m. 91.5-2.5°. 1-Benzyl-3,4-dihydroisoquinoline (V) yields a HCl salt, with 0.5 mol. H2O, m. 227-9°. Distillation of V at atm. pressure gives isoquinoline and a mixture b0.7 145-8°, nD21 1.6252, with 0.33 atom of active H; 1-benzylisoquinoline was identified as the picrate and the HCl salt (with 2 mols. H2O). Absorption maximum are given for these compounds in 0.1 N HCl and EtOH. In the experiment, the researchers used many compounds, for example, 1-Phenyl-3,4-dihydroisoquinoline (cas: 52250-50-7Reference of 52250-50-7).

1-Phenyl-3,4-dihydroisoquinoline (cas: 52250-50-7) belongs to isoquinoline derivatives. Although isoquinoline derivatives can be synthesized by several methods, relatively few direct methods deliver the unsubstituted isoquinoline. They are also used to make oil-soluble dyes, food colorants, pharmaceuticals, pH indicators and other organic compounds. Reference of 52250-50-7

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem