The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《8-(3-Diethylaminopropylamino)isoquinoline》. Authors are Robinson, Richard A..The article about the compound:Isoquinolin-6-olcas:7651-82-3,SMILESS:OC1=CC2=C(C=NC=C2)C=C1).Product Details of 7651-82-3. Through the article, more information about this compound (cas:7651-82-3) is conveyed.
cf. preceding 2 abstracts Isoquinoline sulfate (78 g.), preheated to 300°, treated (5 min.) with 60 g. 60% oleum, and heated 5 min. at 300°, gives 35% of the 5-sulfonic acid (as the Ca salt) and 55 g. of mixed Na isoquinolinesulfonates which, on fusion with NaOH (10 min. at 210°), give 15% 8-hydroxyisoquinoline (I), m. 213° (picrate, m. 285°). I (10 g.), 60 mL. concentrated NH4OH, and 14 g. SO2, heated 6 h. at 150-60°, give 8.5 g. 8-aminoisoquinoline (II), m. 174°. II (20 g.), 120 g. Et2N(CH22)3NH2, 150 mL. H2O, and 30 g. SO2, heated at reflux temperature 36 h. under 3 in. pressure, give 18 g. 8-(3-diethylaminopropylamino)isoquinoline, yellow, m. 231°. 6-Methoxyisoquinoline (0.3 g.) and 20 mL. 48% HBr, refluxed 2 h., give 6-hydroxyisoquinoline, m. 220°; HCl salt m. 175°.
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Reference:
Chapter 1 An introduction to palladium catalysis,
Palladium/carbon catalyst regeneration and mechanical application method