Stannous chloride dihydrate → HCID 19390586, compound
Reaction equation
[CH2:1]([O:4][C:5]([C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([N+:17]([O-])=O)[CH:13]=2)[N:8]=1)=[O:6])[CH:2]=[CH2:3].O.O.Cl[Sn]Cl>CO>[CH2:1]([O:4][C:5]([C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([NH2:17])[CH:13]=2)[N:8]=1)=[O:6])[CH:2]=[CH2:3]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 2-allyloxycarbonyl-6-nitroquinoline (1.25 g; 4.8 mM) in MeOH (20 ml) was added SnCl2.2H2O (7.65 g, 33.6 mM). After stirring at ambient temperature for 3 hours, the mixture was evaporated to dryness and the residue partitioned between an aqueous solution of NH4OH (pH 8.5) and ethyl acetate. The organic phase was concentrated and purified by subjecting to flash chromatography, eluting with ethyl acetate/petroleum ether (65/35) to give 2-allyloxycarbonyl-6-aminoquinoline (280 mg; 28%).