The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Benzoylacetamide and iminobenzoylacetamide》. Authors are Checchi, Silvio; Papini, Piero.The article about the compound:3,5-Dimethyl-4-nitropyridine 1-oxidecas:14248-66-9,SMILESS:O=[N+](C1=C(C)C=[N+]([O-])C=C1C)[O-]).Electric Literature of C7H8N2O3. Through the article, more information about this compound (cas:14248-66-9) is conveyed.
cf. CA 53, 21974b. BzCH2CN (I) was prepared in excellent yields from BzCH2CONH2 (II) and POCl3. Similar treatment of PhC(:NH)CH2CN (III) gave 6,3,2,4-Cl(CN)Ph2C5HN (IV), converted to give various 3,6-disubstituted 2,4-diphenylpyridines, N:CPh:CR:CPh.CH:CR’ (V). II (10 g.) and 18 g. POCl3 heated (H2O-free atm.) 30 min. on a steam bath at 60-70°, the cooled mixture decomposed with cold H2O, and the solid isolated and recrystallized repeatedly from H2O gave crystalline I, m. 70-2°. III (5 g.) and 8 g. POCl3 similarly heated 1 hr. at 70-80°, the cooled mass taken up in cold H2O, the washed (H2O, alc., Et2O) and dried product taken up in alc. containing a trace of HCl, and the crystalline material recrystallized from alc. yielded IV, m. 178-80°. IV (2 g.) refluxed 1 hr. in alc. containing 1 g. KOH and concentrated, the solution neutralized with dilute HCl, and the precipitate recrystallized from alc. gave V (R = CN, R’ = OH), m. 150°. IV (2 g.) heated 4 hrs. at 180° in a sealed tube with excess alc. NH3, the cooled mixture evaporated, and the product separated and recrystallized from ClCH:CCl2 yielded V (R = CN, R’ = NH2) hemihydrate, m. 214-15°. IV (5 g.) refluxed in alc. with powd. Zn, the filtered solution evaporated on a steam bath, and the residue taken up in a min. of HCONMe2 and diluted with H2O gave V(R = CN, R’ = H) (VI), m. 175-7° (alc.). VI (3 g.) heated 6 hrs. at 180-200° with concentrated HCl in a sealed tube, the liquid poured into hot H2O, the filtered solution neutralized with NH4OH, and the precipitate crystallized from alc. gave V(R = CO2H, R’ = H), m. 248-50°, decarboxylated by heating at 250° to V (R = R’ = H), characterized as the sulfate, m. 245° (darkening), and as the picrate, m. 187° (decomposition). IV (3 g.) refluxed 7 hrs. in 40% alc. KOH, the solvent evaporated, and the residue taken up in H2O and acidified with dilute HCl gave V (R = CONH2, R’ = OH), m. 287-9° (alc.), converted by heating 6 hrs. in a sealed tube at 180-90° with concentrated HCl to give V (R = H, R’ = OH), m. 210° (alc.) (also obtained similarly from IV); picrate m. 193-5° (alc.). VI (1 g.) boiled 2-3 min. in 4 ml. dilute H2SO4, the mixture boiled with addition of H2O, the cooled filtered solution made alk. with dilute NH4OH, and the precipitate crystallized from AcOEt and CHCl3 gave V (R = CONH2, R’ = H), m. 225-7°.
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Reference:
Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem