Stannous Chloride → 2-Amino-4-chloro-N-(5-trifluoromethyl-quinolin-8-yl)-benzenesulfonamide

HRID 513562Notes

Reaction equation

HRID 513562 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[CH:13]=[CH:14][C:15]([C:22]([F:25])([F:24])[F:23])=[C:16]3[C:21]=2[N:20]=[CH:19][CH:18]=[CH:17]3)(=[O:10])=[O:9])=[C:4]([N+:26]([O-])=O)[CH:3]=1.Cl[Sn]Cl>Cl.CCO>[NH2:26][C:4]1[CH:3]=[C:2]([Cl:1])[CH:7]=[CH:6][C:5]=1[S:8]([NH:11][C:12]1[CH:13]=[CH:14][C:15]([C:22]([F:24])([F:25])[F:23])=[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 681831454-Chloro-2-nitro-N-(5-trifluoromethyl-quinolin-8-yl)-benzenesulfonamide2×

Product 1

HCID 681833502-Amino-4-chloro-N-(5-trifluoromethyl-quinolin-8-yl)-benzenesulfonamideYield 98.4%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 702EthanolSolvent

Procedure

In a similar fashion using route 1 general procedure 4, 4-chloro-2-nitro-N-(5-trifluoromethyl-quinolin-8-yl)-benzenesulfonamide (Intermediate 254) (370 mg, 0.86 mmol), SnCl2 (967 mg, 5.15 mmol), conc.HCl (4-5 drops) and EtOH (15 ml) gave the title compound (340 mg, 98%) which was used in the next step without further purification.

Sources & evidence

ORD record
ord-c1a0da29c6d94c28aa086aaa699ca013
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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