The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Selective reduction of 2,2′,4,4′-tetranitrobiphenyl》. Authors are Bailey, William J..The article about the compound:Isoquinolin-6-olcas:7651-82-3,SMILESS:OC1=CC2=C(C=NC=C2)C=C1).Application In Synthesis of Isoquinolin-6-ol. Through the article, more information about this compound (cas:7651-82-3) is conveyed.
Adding (1 hr.) 152 g. Na2S and 48 g. NaHCO3 in 400 cc. warm H2O to 67 g. [2,4-(O2N)2C6H3]2, m. 163-4°, in 2.5 l. boiling MeOH with stirring and avoiding a large excess of Na2S throughout the reaction, and concentrating the filtered solution give 2 crops totaling 62% 2,2′-dinitrobenzidine, m. 212-14° [N,N’-Ac2 derivative, 81%, m. 292-3° (decomposition)], identical with that obtained on nitration of benzidine with NaNO3 and H2SO4 according to Tauber [Ber. 28, 379(1890)].
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Reference:
Chapter 1 An introduction to palladium catalysis,
Palladium/carbon catalyst regeneration and mechanical application method