Most of the compounds have physiologically active properties, and their biological properties are often attributed to the heteroatoms contained in their molecules, and most of these heteroatoms also appear in cyclic structures. A Journal, Yakugaku Zasshi called Nitration of isoquinoline 2-oxide, Author is Ochiai, Eiji; Ikehara, Morio, which mentions a compound: 152814-23-8, SMILESS is NC1=CC=CC2=C1C=CN=C2.[H]Cl, Molecular C9H9ClN2, SDS of cas: 152814-23-8.
Isoquinoline 2-oxide (I) (5 g.) in 20 g. concentrated H2SO4 and 5 g. KNO3, heated 3 hrs. at 60°, the mixture poured into ice water, made alk. with Na2CO3, and the product recrystallized from Me2CO give 4.5 g. 5-nitroisoquinoline 2-oxide (II), yellow needles, m. 220°. Chromatographic separation of the mother liquor in C6H6 gives 0.1 g. C9H6O3N2 (III), m. 179-80°. III (0.1 g.) in 10 ml. CHCl3 heated 10 min. at 50° with 1 ml. PCl3, let stand 3 hrs., the product poured into ice water, and the mixture made alk. with Na2CO3 and extracted with CHCl3 gives 0.1 g. C9H6O2N2 (IV), needles, m. 70°; catalytic reduction of 70 mg. IV in 10 ml. alc. with Pd-C (1 ml. 1% PdCl2 and 0.2 g. C) gives 70 mg. sirupy product (IVA), which, diazotized in 2 ml. 15% HCl at 0-2° with 20 mg. NaNO2 in 0.5 ml. water, and the solution poured into Cu2Cl2 (0.2 g. CuCl2, 1 ml. water, 0.5 ml. concentrated HCl, and 0.1 g. Zn), made alk. with Na2CO3, and extracted with Et2O, gives 8-chloroisoquinoline (V), needles, m. 55°; picrate, m. 190°. Catalytic reduction of 0.5 g. II in 40 ml. alc. with 0.2 g. Pd-C (60%), 10 ml. 10% HCl, and H gives 0.3 g. 5-aminoisoquinoline (VI), needles, m. 124-5°; picrate, m. 226-8°; VI.HCl, m. 270° (decomposition); VI acetate, m. 145-6°. The mother liquor from VI in C6H6 passed through Al2O3 gives a small amount of 5-amino-1,2,3,4-tetrahydroisoquinoline (VII), prisms, m. 150-1°; HCl salt, m. 308-9°, picrate, m. 205-6° (decomposition). VII (50 mg.) in 1 ml. Ac2O and a small amount of AcONa heated 2 hrs. at 100°, the Ac2O removed in vacuo, and the residue made alk. with Na2CO3 and extracted with Et2O gives 40 mg. 5-acetamido-2-acetyl-1,2,3,4-tetrahydroisoquinoline, needles, m. 155-6° (from C6H6). Catalytic reduction of 0.5 g. II in 40 ml. alc. with 0.2 g. Pd-C (60%) and H 70 min. gives 0.4 g. VI and 0.1 g. 5-aminoisoquinoline 2-oxide (VIII), needles, m. 225°. VIII (0.1 g.) in 10 ml. CHCl3 and 1 ml. PCl3 refluxed 30 min. on a water bath, and the mixture cooled, made alk. with Na2CO3, and extracted with CHCl3 gives 70 mg. VI. VI (0.2 g.) in 5 ml. 20% NaHSO3 heated 6 hrs. at 150° in a sealed tube, the product made alk. with NaOH, extracted with C6H6, the aqueous layer acidified with HCl, evaporated to dryness, the residue taken up with a small amount of water, the solution saturated with Na2CO3, and the precipitate recrystallized from alc. gives 0.1 g. 5-hydroxyisoquinoline, prisms, m. 230° (decomposition).
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Reference:
1,8-Naphthyridine – Wikipedia,
1,8-Naphthyridine | C8H6N2 – PubChem