Stannous Chloride → 2-Amino-N-quinolin-8-yl-4-trifluoromethoxy-benzenesulfonamide

HRID 513580Notes

Reaction equation

HRID 513580 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([O:10][C:11]([F:14])([F:13])[F:12])[CH:7]=[CH:6][C:5]=1[S:15]([NH:18][C:19]1[CH:20]=[CH:21][CH:22]=[C:23]2[C:28]=1[N:27]=[CH:26][CH:25]=[CH:24]2)(=[O:17])=[O:16])([O-])=O.Cl[Sn]Cl>Cl.CCO>[NH2:1][C:4]1[CH:9]=[C:8]([O:10][C:11]([F:13])([F:12])[F:14])[CH:7]=[CH:6][C:5]=1[S:15]([NH:18][C:19]1[CH:20]=[CH:21][CH:22]=[C:23]2[C:28]=1[N:27]=[CH:26][CH:25]=[CH:24]2)(=[O:16])=[O:17]

Participants

5

Reactant 2

HCID 24479Stannous ChlorideHCID 681832432-Nitro-N-quinolin-8-yl-4-trifluoromethoxy-benzenesulfonamide2×

Product 1

HCID 681833742-Amino-N-quinolin-8-yl-4-trifluoromethoxy-benzenesulfonamideYield 75.5%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 702EthanolSolvent

Procedure

In a similar fashion using route 1 general procedure 4, 2-nitro-N-quinolin-8-yl-4-trifluoromethoxy-benzenesulfonamide (Intermediate 271) (500 mg, 1.21 mmol), SnCl2 (918 mg, 4.84 mmol), 6N HCl (5 drops) and EtOH (10 ml) gave the title compound (350 mg, 75%) which was used in the next step without further purification.

Sources & evidence

ORD record
ord-7c7c9b0ca139424c8fcadec6d0d0c2ac
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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