Stannous Chloride → HCID 58118774, compound
Reaction equation
[F:1][C:2]1[C:8]([O:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:7][CH:6]=[C:5]([N+:16]([O-])=O)[C:3]=1[NH2:4].[Sn](Cl)Cl>CO>[F:1][C:2]1[C:8]([O:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:7][CH:6]=[C:5]([NH2:16])[C:3]=1[NH2:4]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 2-fluoro-6-nitro-3-phenoxyaniline (260 mg, 1.05 mmol) in methanol (20 ml) was added tin(II)chloride (1.18 g, 5.24 mmol). The reaction was heated to reflux overnight and then cooled to rt. The mixture was concentrated under reduced pressure and the residue was dissolved in ethyl acetate (50 mL). The solution was poured into an aqueous saturated sodium bicarbonate solution (150 mL), causing a precipitate to crash out. The mixture was filtered using ethyl acetate to rinse. The filtrate was washed with water and brine, dried over sodium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel chromatography using 0-70% ethyl acetate/hexane to yield the desired product (195 mg, 85%) 1H NMR (300 MHz, DMSO-d6) 7.22-7.31 (m, 2H), 6.94-7.01 (m, 1H), 6.82 (d, J=7.8 Hz, 2H), 6.31 (dd, J=8.5, 1.5 Hz, 1H), 6.20 (dd, J=8.5, 8.5 Hz, 1H); ES-MS m/z 219.3 (MH)+; HPLC RT (Method A) 2.40 min.