Stannous Chloride → 2-Amino-N-(4-trifluoromethyl-quinolin-8-yl)-benzenesulfonamide

HRID 513559Notes

Reaction equation

HRID 513559 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][CH:17]=[C:18]2[C:23]=1[N:22]=[CH:21][CH:20]=[C:19]2[C:24]([F:27])([F:26])[F:25])(=[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][CH:17]=[C:18]2[C:23]=1[N:22]=[CH:21][CH:20]=[C:19]2[C:24]([F:27])([F:26])[F:25])(=[O:12])=[O:11]

Participants

5

Reactant 2

HCID 24479Stannous ChlorideHCID 681833412-Nitro-N-(4-trifluoromethyl-quinolin-8-yl)-benzenesulfonamide2×

Product 1

HCID 681834872-Amino-N-(4-trifluoromethyl-quinolin-8-yl)-benzenesulfonamideYield 81.7%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 702EthanolSolvent

Procedure

In a similar fashion using route 1 general procedure 4, 2-nitro-N-(4-trifluoromethyl-quinolin-8-yl)-benzenesulfonamide (Intermediate 251) (0.4 g, 1.0 mmol), SnCl2 (0.76 g, 4.03 mmol), 6N HCl (2 drops) and EtOH (15 ml) gave the title compound (300 mg, 81%) which was used in the next step without further purification.

Sources & evidence

ORD record
ord-d495ee170e7744a8acffbdb0a91b5f6f
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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