Stannous Chloride → N4-(3-ethynylphenyl)quinazoline-4,7-diamine
Reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([NH:9][C:10]2[C:19]3[C:14](=[CH:15][C:16]([N+:20]([O-])=O)=[CH:17][CH:18]=3)[N:13]=[CH:12][N:11]=2)[CH:6]=[CH:7][CH:8]=1)#[CH:2].Cl[Sn]Cl>C(OCC)(=O)C>[C:1]([C:3]1[CH:4]=[C:5]([NH:9][C:10]2[C:19]3[C:14](=[CH:15][C:16]([NH2:20])=[CH:17][CH:18]=3)[N:13]=[CH:12][N:11]=2)[CH:6]=[CH:7][CH:8]=1)#[CH:2]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
N-(3-ethynylphenyl)-7-nitroquinazolin-4-amine (2.0 g, 6.89 mmol), SnCl2 (5.0 g, 26.37 mmol), and ethyl acetate (50 mL) was refluxed for 3 h. The mixture was subjected to extraction with ethyl acetate (20 mL). The combined organic layers were washed with brine (20 mL×2), dried over Na2SO4, and concentrated in vacuo to afford 1.6 g (86%) of N4-(3-ethynylphenyl)quinazoline-4,7-diamine as a yellow solid.