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
A mixture of 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, and then subeject to extraction with ethyl acetate (20 mL) twice. The combined organic layers were washed with brine (20 mL) twice, 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.