Stannous Chloride → 6-Amino-2-(3,4-methylendioxy-phenyl)quinazoline
Reaktionsgleichung
[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]=[C:9]([C:14]1[CH:22]=[CH:21][C:17]3[O:18][CH2:19][O:20][C:16]=3[CH:15]=1)[N:8]=[CH:7]2)([O-])=O.Cl[Sn]Cl>C(O)C>[NH2:1][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]=[C:9]([C:14]1[CH:22]=[CH:21][C:17]3[O:18][CH2:19][O:20][C:16]=3[CH:15]=1)[N:8]=[CH:7]2Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
A suspension of 6-nitro-2-(1,3-benzodioxol-5-yl)-quinazoline (37 g, 0.126 mol) and SnCl2 2H2O (117.2 g, 0.504 mol) in ethanol (500 ml) was heated at reflux for 1 h. After cooling to r.t., the solvent was removed i.v., chloroform was added and the mixture was basified with ammonia. The precipitate was filtered off and washed with chloroform. The filtrates were collected, washed with water and dried over Na2SO4. The solution was concentrated i.v., and the residue triturated with diisopropyl ether/petroleum ether. The solid was filtered and dried i.v. to give the titled product (21.2 g, 64% yield). C15H11N3O2, MW: 265.27. mp 191-192° C.; 1H NMR (DMSO-d6) 9.24 (s, 1H), 8.05 (dd, 1H), 7.91 (d, 1H), 7.73 (d, 1H), 7.39 (dd, 1H), 7.03 (d, 1H), 6.90 (d, 1H), 6.11 (s, 2H), 5.93 (s, 2H); IR (KBr) 3319, 3203, 1631, 1500, 1446; TLC (CHCl3/MeOH 9/1) Rf=0.3.