1-(Dialkylaminoalkylamino)isoquinolines was written by Robinson, Richard A.. And the article was included in Journal of the American Chemical Society in 1947.Reference of 23707-37-1 This article mentions the following:
1-Chloroisoquinoline (I) (16.3 g.) and 35 g. Et2N(CH2)3NH2 heated 10 min. at 135-40°, the temperature raised to 175-80° during 25 min., and held at that point 10 min., give 88% 1-(3-diethylamino-propylamino)isoquinoline-2HCl, m. 125°. The following analogs were prepared similarly: 1-(1-diethylaminobutylamino), m. 90°, 85%; 1-(1-diethylamino-1-methylbutylamino), m. 95-100°, 80%; 1-(3-dibutylaminopropylamino) , m. 135°, 85%; 1-(3-dihexylaminopropylamino), m. 163°, 80%; 1-[3-(3-diethylaminopropylamino)propylamino](tri-HCl salt), m. 140°, 60%; 5-methoxy-1-(3-diethylaminopropylamino), m. 231°, 85%; 6-methoxy-1-(3-diethylaminopropylamino), m. 184°, 85%; 7-methoxy-1-(3-diethylaminopropylamino), m. 120°, 80%; 5-chloro-1-(3-diethylaminopropylamino) , m. 227°, 75%; 7-Cl isomer, m. 161°, 80%; 3-Cl isomer, m. 125°, 75%; 1-(7-diethyl-aminoheptylamino) (free base), oil, 80%. 6-Methoxy-tetrahydroisoquinoline (20 g.), 35 g. Raney Ni, and 200 g. C10H8, heated 1 hr. at 200 ± 5°, give 95% 6-methoxyisoquinoline (II), whose HCl salt m. 216°; picrate m. 225°. I (40 g.), added slowly to 0.328 mole perphthalic acid in 1300 ml. ether at -6 to -8°, the mixture stirred 90 min., kept overnight at 0°, the oily perphthalate washed with ether, and allowed to stand overnight at room temperature, gives 40% of the N-oxide (III), whose HCl salt m. 197°. With POCl3 III yields 70% 6-methoxy-1-chloroisoquinoline, m. 77°. 7-Hydroxyisoquinoline by the Bucherer reaction yields 95% 7-aminoisoquinoline, m. 204°; through the diazo reaction it yields 75% 7-chloroisoquinoline (IV), m. 45°; 47 g. IV was added to a mixture of 41.14 g. 30% H2O2 and 200 ml. AcOH (after heating 1 hr. on the steam bath) and the solution heated 1 hr. on the steam bath to give 97% of the N-oxide (V), whose HCl salt m. 218°; with POCl3 V yields 90% 1,7-dichloroisoquinoline, m. 138°. Fusion of Na 5-isoquinolinesulfonate with KOH at 220-30° (15 min.) gives 90% 1,5-dihydroxyisoquinoline, m. 282°; MeI yields 50% of the 5-methoxy-1-hydroxy derivative, m. 220°; POCl3 gives 70% of the 5-Methoxy-1-chloro derivative, m. 137°. 7-Methoxyisoquinoline N-oxide with POCl3 yields 75% of the 7-methoxy-1-chloro derivative, m. 176°. I and HNO3 in H2SO4 at 5-8° give 80% 1-chloro-5-nitroisoquinoline, m. 187°; reduction over Raney Ni at 25°/3 atm. gives 75% of the 5-NH2 derivative, m. 180°; the diazo reaction yields 50% 1,5-dichloroisoquinoline, m. 147°. In the experiment, the researchers used many compounds, for example, Isoquinolin-7-amine (cas: 23707-37-1Reference of 23707-37-1).
Isoquinolin-7-amine (cas: 23707-37-1) belongs to isoquinoline derivatives. Quinoline and isoquinoline skeletons are among the most attractive frameworks with a wide range of biological and pharmacological activities. Isoquinoline-type alkaloids show biological activities similar to those of morphinane-, protoberberine-, and benzophenanthridine-type alkaloids.Reference of 23707-37-1
Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem