Stannous Chloride → 2-Amino-5-fluoro-N-quinolin-8-yl-benzenesulfonamide

HRID 513576Notes

Reaction equation

HRID 513576 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:22]([O-])=O)=[C:6]([S:8]([NH:11][C:12]2[CH:13]=[CH:14][CH:15]=[C:16]3[C:21]=2[N:20]=[CH:19][CH:18]=[CH:17]3)(=[O:10])=[O:9])[CH:7]=1.Cl[Sn]Cl>Cl.CCO>[NH2:22][C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:7][C:6]=1[S:8]([NH:11][C:12]1[CH:13]=[CH:14][CH:15]=[C:16]2[C:21]=1[N:20]=[CH:19][CH:18]=[CH:17]2)(=[O:9])=[O:10]

Participants

5

Reactant 2

HCID 24479Stannous ChlorideHCID 681832775-Fluoro-2-nitro-N-quinolin-8-yl-benzenesulfonamide2×

Product 1

HCID 681831462-Amino-5-fluoro-N-quinolin-8-yl-benzenesulfonamideYield 111.8%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 702EthanolSolvent

Procedure

In a similar fashion using route 1 general procedure 4, 5-fluoro-2-nitro-N-quinolin-8-yl-benzenesulfonamide (Intermediate 267) (0.60 g, 1.72 mmol), SnCl2 (1.31 g, 6.91 mmol), 6N HCl (6 drops) and EtOH (7 ml) gave the title compound (610 mg) which was used in the next step without further purification.

Sources & evidence

ORD record
ord-2ca01afc330d4e04b869fc7bda33496b
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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