The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Chemistry of the benz-α,β-isoxazoles》. Authors are Lindemann, Hans; Thiele, Hans.The article about the compound:1,2-Benzisoxazolecas:271-95-4,SMILESS:C12=CC=CC=C1ON=C2).Electric Literature of C7H5NO. Through the article, more information about this compound (cas:271-95-4) is conveyed.
5,2-O2N(Cl)C6H3CH:NOH in EtOH is unchanged by heating 0.25 hr. with aqueous AcON3 or with Ag2O; alkalies give yellow, salts which yield the oxime on acidifying; the oxime is also unchanged after heating in C5H5 or PhNO2, but, heated dry, decomposes violently. Heated with EtOH-KOH, it gives 2,5-HO(O2N)-C5H3CN (I), which also results from nitro-4-indoxazene and 10% NaOH or upon nitrating o-HOC6H4CN. Heating I above its m. p. for a short time gives 2,4,6-tri-[2-hydroxy-5-nitrophenyl]-l,3,5-triazine, yellow, m. above 340°; Ac2O and H2SO4 gradually dissolve it but no Ac derivative could be isolated. The corresponding 3,5-dibromo derivative, yellow, m. 355°, results from 3,5,2-Br2(HO)C6H2CN (II). 3,5-Dibromosalicylaldoxime (III), m. 218-20°; solution in warm Ac2O gives the mono-Ac derivative, m. 146°; heated above its m. p., it gives II; Ac2O and H2SO4, give the di-Ac derivative m. 150°. III, boiled with Ac2O for 2 hrs., gives 3,5-dibromo-2-acetoxybenzonitrile, m. 85-7°. 2-Hydroxybenzaldehyde acetyloxime, m. 75°; slowly heated to 120-30°, it splits off AcOH, giving indoxazene (IV), b14 82-3°, d421 1.1727, nD20 1.5570, MD 32.67; this is probably identical with the compound of Conduché (C. A. 2, 999) from o-HOC6H4CHO and H2NCONHOH. With 40% KOH, IV gives o-NCC6H4OK. 4-Nitro derivative, m. 126°; heated above its m. p., it gives 5,2-O2N(HO)C6H3CN. 2-Hydroxyacetophenoneaceloxime, m. 146°; heated at 160° it gives 2-methylindoxazene, b11 92.5°, d420 1.1247, nD20 1.5483, MD 37.68; 4-NO2 derivative, m. 128°; 4-NH2 derivative, m. 105° (Ac derivative, m. 156°); the diazo solution couples with β-C10H7OH to give a red azo dye. 3-Methyl-6-hydroxyacelophenone acetoxime, m. 114°; heated at 120° it gives 2,4-dimethylindoxazene, b13 116° d420 1.0949, nD20 1.5455, MD 42.45. NO2 derivative, pale yellow, m. 72°.
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