Heterocyclic compounds. I. Synthesis of aminoisoquinoline derivatives was written by Okano, Teisuke;Goya, Shujiro;Tsuda, Yoshinao. And the article was included in Yakugaku Zasshi in 1966.Synthetic Route of C9H7ClN2 This article mentions the following:
A new method for the synthesis of 3-aminoisoquinoline derivatives was proposed where Me o-cyanomethylbenzoate (I) was treated with aqueous amine under mild conditions to give an isoquinoline ring with NH2 group in 3-position. Thus, 20 g. o-carboxyphenylacetonitrile is added to an ethereal solution of 5.6 g. CH2N2, the whole kept overnight, AcOH added, evaporated, and the residue distilled in vacuo to give 19 g. I, b2 135-7°, m. 48.5-49° (MeOH). Methylation of o-cyanomethylbenzoic acid also gave I. I (4 g.) and 50 ml. 28% NH4OH are heated in a sealed tube at 50-60° for 40 hrs. to give 1.8 g. 3-aminoisocarbostyril (II), m. 265° (decomposition) (MeOH); diacetate m. 177°; benzoate m. 271-2°. Similar treatment of I with MeNH2 gives 2-methyl-3-aminoisocarbostyril, m. 188° (EtOH). II (1 g.) is refluxed 3 hrs. with 11 ml. POCl3, an excess of POCl3 removed in vacuo, the residue poured into iced H2O, and the mixture made alk. with 10% NaOH and distilled with steam to give 0.9 g. 1-chloro-2-aminoisoquinoline (III), yellow plates, m. 147-8°. Catalytic reduction of 0.2 g. III in EtOH (containing KOH) using 10% Pd-C gives 0.1 g. 3-aminoisoquinoline, yellow needles, m. 177-8° (C6H6). Heating of 3 g. 1,3-dichloroisoquinoline in a sealed tube at 175° 6 hrs. with 50 ml. 28% NH4OH and a small amount of CuSO4 gives 2.8 g. 1-amino-3-chloroisoquinoline, m. 154-5° (EtOH) which is further subjected to catalytic reduction to give 1-aminoisoquinoline, m. 122-3° (C6H6); picrate m. 280°. In the experiment, the researchers used many compounds, for example, 3-Chloroisoquinolin-1-amine (cas: 7574-67-6Synthetic Route of C9H7ClN2).
3-Chloroisoquinolin-1-amine (cas: 7574-67-6) belongs to isoquinoline derivatives. Although isoquinoline derivatives can be synthesized by several methods, relatively few direct methods deliver the unsubstituted isoquinoline. Isoquinoline-type alkaloids show biological activities similar to those of morphinane-, protoberberine-, and benzophenanthridine-type alkaloids.Synthetic Route of C9H7ClN2
Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem