Chlorosuccinimide → 8-amino-5-chloro-7-methoxy-3,4-dihydroisoquinolin-1(2H)-one
Reaktionsgleichung
[Cl:1]N1C(=O)CCC1=O.[NH2:9][C:10]1[C:11]([O:21][CH3:22])=[CH:12][CH:13]=[C:14]2[C:19]=1[C:18](=[O:20])[NH:17][CH2:16][CH2:15]2>CN(C)C=O>[NH2:9][C:10]1[C:11]([O:21][CH3:22])=[CH:12][C:13]([Cl:1])=[C:14]2[C:19]=1[C:18](=[O:20])[NH:17][CH2:16][CH2:15]2Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
N-chlorosuccinimide (20 g, 0.147 mol) was added to a solution of 8-amino-7-methoxy-3,4-dihydroisoquinolin-1(2H)-one (296c, 24 g, 0.125 mol) in N,N-dimethylformamide (250 mL) and stirred at room temperature overnight. The solution was partitioned between water (100 mL) and ethyl acetate (5×100 mL). The combined organic extracts were washed with brine (5×100 mL), dried over sodium sulfate, and concentrated to dryness. The residue was triturated with acetonitrile (200 mL), and the solids collected by filtration. After drying, 8-amino-5-chloro-7-methoxy-3,4-dihydroisoquinolin-1(2H)-one (296d, 12.5 g, 44% yield) was obtained as a blue solid. 1H NMR (400 MHz, DMSO-d6): δ 7.84 (s, 1H), 6.93 (s, 1H), 3.80 (s, 3H), 3.29-3.25 (m, 2H), 2.81-2.78 (t, J=6.6 Hz, 2H).