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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, Zhurnal Obshchei Khimii called Synthesis and study of N-oxides of heterocyclic compounds. I. N-Oxides of derivatives of morphine, tetra-hydroisoquinoline, and quinoline, Author is Khaletskii, A. M.; Pesin, V. G.; Tsin, Chshou, which mentions a compound: 1127-45-3, SMILESS is OC1=CC=CC2=CC=C[N+]([O-])=C12, Molecular C9H7NO2, Quality Control of 8-Hydroxyquinoline 1-oxide.
cf. Ochiai, C.A. 48, 3359i. Heating 8.4 g. codeine with 45 ml. 3% H2O2 at 50-60° gave after evaporation 8 g. codeine N-oxide, m. 206-8° (H2O); HCl salt, m. 214-17° (EtOH). To 5 g. dihydrohydroxycodeinone-HCl was added 10 ml. 10% NaOH yielding 93% dihydrohydroxycodeinone, m. 213-16°, which with 3% H2O2 as above gave 46.2% dihydrohydroxycodeinone N-oxide, decompose 152-3°, which gives a red color with Ac2O; picrate, m. 190-2°; HCl salt, m. 167-8°. The oxide treated with SO2 in warm EtOH gave 62.5% C18H23O8NS, decompose 169-70°, which was evidently an isomer of dihydrohydroxycodeinone sulfate; with BaCl2 solution it readily gave BaSO4; hydrolysis with 10% NaOH gave the original dihydrohydroxycodeinone, m. 207-9° (sulfate, m. 138-9°). Salsolidine (3 g.) in 20 ml. Me2CO and 30 ml. H2O treated with 2.5 ml. 30% H2O2 after several days at room temperature gave 15.48% N-hydroxysalsolidine, m. 100-1° (aqueous EtOH), which reduced Fehling and Tollens reagents. Similarly, N-methylsalsolidine gave N-methylsalsolidine N-oxide picrate, m. 133-4° (aqueous EtOH); HCl salt analog, decompose 162-3°. Oxidation of salsoline with 3% H2O2 in AcOH or with BzO2H in CHCl3 either gave no reaction or failed to yield any definite products. N-Methylsalsoline with aqueous H2O2 at room temperature in 3 days gave N-methylsalsoline N-oxide, m. 183° (EtOH); HCl salt, m. 186°. Oxidation of 8-hydroxyquinoline in CHCl3 with BzO2H with cooling gave yellow 8-hydroxyquinoline N-oxide, m. 137-8° (H2O); the same formed on oxidation with 30% H2O2 in AcOH-Ac2O at 40-5° in 3 hrs., but with 30% H2O2-AcOH in 2 hrs. only the starting material was recovered. 8-Hydroxyquinoline N-oxide treated with alc. KOH and Etl at reflux gave 8-ethoxyquinoline N-oxide, isolated as picrate, m. 135-8°; the same formed on treatment of 8-ethoxyquinoline with AcOH-Ac2O-30% H2O2 at 45-50°; HCl salt, m. 158°; free oxide, m. 61-2°. Similarly 2-phenylquinoline-4-carboxylic acid and AcOH-H2O2 gave 76% N-oxide, m. 244°, and 15% benzoylanthranilic acid, m. 170-2°. Oxidation of 2-phenylquinoline-4-carboxylic acid with BzO2H in CHCl3 in 2 days gave no evident reaction, the same being true of oxidation with 25% H2O2 in EtOH-Me2CO at 50°. Reduction of 2-phenylquinoline-4-carboxylic acid N-oxide with Na hydrosulfite in aqueous EtOH gave the original 2-phenylquinoline-4-carboxylic acid, m. 205-7°.
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Reference:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider