The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《8-Hydroxy-1-methoxyquinoline methosulfate》. Authors are Krasavin, I. A.; Dziomko, V. M.; Radin, Yu. P..The article about the compound:8-Hydroxyquinoline 1-oxidecas:1127-45-3,SMILESS:OC1=CC=CC2=CC=C[N+]([O-])=C12).Synthetic Route of C9H7NO2. Through the article, more information about this compound (cas:1127-45-3) is conveyed.
The crude title compound, not described previously, m. 126-8° (decomposition) and is very soluble in water, soluble in alcs., and insoluble in nonpolar solvents. Reaction with nucleophilic compounds gives 2-substituted 8-hydroxyquinolines. A mixture of 48.3 g. powd. 8-hydroxyquinoline 1-oxide (m. 138.5-39°) (Phillips, et al., CA 51, 11349a; Murase and Demura, CA 58 3390b, recrystallized twice from water and C6H6) and 37.9 g. freshly distilled Me2SO4 is warmed on a water bath 2 hrs. with reflux. The mass is cooled and stirred until crystallization, 200 ml. dry Et2O is added, and the mixture stirred until all material is hardened. The solid is washed with 50-100 ml. Et2O in a mortar after filtration, washed on the filter with Et2O, and dried in a vacuum desiccator. Yield 77.6-9.3 g. hygroscopic material. Recrystallization of 20 g. from EtOH-Et2O gave 3.67 g., m. 143-4.5°.
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Reference:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider