Benzyl (3-aminopropyl)carbamate → 4-[3-(Benzyloxycarbonylamino)propylamino]-2-chloro-3-nitroquinoline
Reaktionsgleichung
[Cl:1][C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[C:10](Cl)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[CH2:16]([O:23][C:24]([NH:26][CH2:27][CH2:28][CH2:29][NH2:30])=[O:25])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C(N(CC)CC)C>[CH2:16]([O:23][C:24]([NH:26][CH2:27][CH2:28][CH2:29][NH:30][C:10]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=[C:2]([Cl:1])[C:11]=1[N+:12]([O-:14])=[O:13])=[O:25])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
0.19 g (0.768 mmol) of 2,4-dichloro-3-nitroquinoline and 0.16 g (0.768 mmol) of N-(benzyloxycarbonyl)-1,3-propanediamine was heated at 70° C. in 5 ml of triethylamine for one hour with stirring. After triethylamine was distilled off under reduced pressure, the residue was dissolved in methylene chloride, washed with water, and dried (MgSO4). The solvent was distilled off under reduced pressure and the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=2:1 (v/v)) to obtain 0.27 g (0.651 mmol) of 4-[3-(benzyloxycarbonylamino)propylamino]-2-chloro-3-nitroquinoline shown below as yellow powder. ##STR29## Its spectroscopic data are as follows: 1H-NMR (CDCl3) δ (ppm) :1.79 (2H, m), 3.35 (4H, m), 5.02 (1H, br), 5.18 (2H, s), 7.15 (1H, br), 7.37 (5H, m), 7.57 (1H, t, J=8.0 Hz), 7.73 (1H, t, J=7.8 Hz), 7.90 (1H, d, J=8.4 Hz), 8.21 (1H, d, J=8.0 Hz).