Synthesis of some isoquinolines was written by Manske, Richard H. F.;Kulka, Marshall. And the article was included in Canadian Journal of Research, Section B: Chemical Sciences in 1949.Recommanded Product: 23707-37-1 This article mentions the following:
5-Chloroisoquinoline (I), m. 73-4° (all m. ps. corrected) (60% yield), and the 7-isomer (II) (cf. Robinson, C.A. 41, 6886h) (perchlorate, m. 163-4°) were prepared by the Sandmeyer reaction from the 5-NH2 compound (III) (cf. Misani and Bogert, C.A. 40, 1845.8) and the 7-NH2 compound (IV) (cf. R., loc. cit.), resp. The Ac derivative (V) of IV m. 147-8°; hydrate m. 103-4°. A better yield of IV was obtained when the Schiff base (cf. Woodward and Doering, C.A. 39, 3002.3) was purified before cyclization. The diazotized III and IV, reduced with SnCl2, yielded 51% 5-and 50% of the 7-NH2NH compound, m. 165-7° and 158-60°. m-ClC6H4CHO and NH2CH2CH-(OEt)2 (VI) (25 g. each), heated on the steam bath 0.5 hr. and distilled, yielded 86% of the Schiff base, b11 170°. The ring was closed with H2SO4 and P2O5 (cf. Tyson, C.A. 33, 1736.9); the yield of mixed I and II was 38%. Nitration of I and II yielded 87% of the 5-VII and 86% of the 7-chloro-8-nitro compound (VIII), m. 134-5° and 146-7°. VII and VIII with SnCl2 in concentrated HCl yielded 75% of the 5- and 55% of the 7-chloro-8-amino compound, m. 204-5° and 171-2° VII and VIII with alc. NH3 yielded the 5-(IX) and the 7-amino-8-nitro compound (X), m. 265-8° (decomposition) (Ac derivative, m. 225-7°) and 246-7° (65% yield). Deamination of the diazotized X with H3PO2 yielded 8-chloroisoquinoline (XI) (cf. Keilin and Cass, C.A. 37, 129.3). Reduction of diazotized IX and X yielded 80% of the 8-hydrazino-5-chloro and 56% of the 7-hydrazino-8-chloro compound, m. 192-3° (decomposition) and 176-8°. Chlorination of V (1 g.) yielded 0.7 g. of the 7-acetamido-8-chloro compound (XII), m. 166-7°. XII (0.5 g.) yielded 0.40 g. of the 7-amino-8-chloro compound (XIII), m. 177-9°. Deamination of XIII gave XI. VI and 2,3-Cl(HO)C6H3CHO (15 g. each) were heated 0.5 hr. on the steam bath, dried by repeated C6H6 distillations, the ring closed with 76% H2SO4 at 0°, the mixture stirred 4 hrs. at 2-5°, allowed to stand 40 hrs. at 8°, and 30 hrs. at room temperature, dissolved in H2O, NH4OH and Na2CO3 added, and the precipitate filtered and sublimed at 175° (1 mm.) to yield 64% of the 7-hydroxy-8-chloro compound (XIV), m. 230-1°. The Bucherer reaction yielded IV, m. 203-4°, with XIV. In the experiment, the researchers used many compounds, for example, Isoquinolin-7-amine (cas: 23707-37-1Recommanded Product: 23707-37-1).
Isoquinolin-7-amine (cas: 23707-37-1) belongs to isoquinoline derivatives. The isoquinoline structure occurs in a considerable number of alkaloids in widely separated plant families. Isoquinoline-type alkaloids show biological activities similar to those of morphinane-, protoberberine-, and benzophenanthridine-type alkaloids.Recommanded Product: 23707-37-1
Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem