Stannous Chloride → 2-Amino-N-(5-trifluoromethyl-quinolin-8-yl)-benzenesulfonamide

HRID 513561Notes

Reaction equation

HRID 513561 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10]([NH:13][C:14]1[CH:15]=[CH:16][C:17]([C:24]([F:27])([F:26])[F:25])=[C:18]2[C:23]=1[N:22]=[CH:21][CH:20]=[CH:19]2)(=[O:12])=[O:11])([O-])=O.Cl[Sn]Cl>Cl.CCO>[NH2:1][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10]([NH:13][C:14]1[CH:15]=[CH:16][C:17]([C:24]([F:27])([F:26])[F:25])=[C:18]2[C:23]=1[N:22]=[CH:21][CH:20]=[CH:19]2)(=[O:12])=[O:11]

Participants

5

Reactant 2

HCID 24479Stannous ChlorideHCID 681832412-Nitro-N-(5-trifluoromethyl-quinolin-8-yl)-benzenesulfonamide2×

Product 1

HCID 681834522-Amino-N-(5-trifluoromethyl-quinolin-8-yl)-benzenesulfonamideYield 90.7%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 702EthanolSolvent

Procedure

In a similar fashion using route 1 general procedure 4, 2-nitro-N-(5-trifluoromethyl-quinolin-8-yl)-benzenesulfonamide (Intermediate 253) (275 mg, 0.69 mmol), SnCl2 (526 mg, 3.46 mmol), conc.HCl (5 drops) and EtOH (10 ml) gave the title compound (230 mg, 90%) which was used in the next step without further purification.

Sources & evidence

ORD record
ord-c195fe4ceb9440218a9a72289151156e
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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