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

HRID 513560
Notes
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Reaction equation

HRID 513560 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([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]=[C:17]3[C:22]([F:25])([F:24])[F:23])(=[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][CH:15]=[C:16]2[C:21]=1[N:20]=[CH:19][CH:18]=[C:17]2[C:22]([F:24])([F:25])[F:23])(=[O:9])=[O:10]
ParticipantsProcedureSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 24479Stannous ChlorideHCID 681831994-Chloro-2-nitro-N-(4-trifluoromethyl-quinolin-8-yl)-benzenesulfonamide2×

Product 1

HCID 681830022-Amino-4-chloro-N-(4-trifluoromethyl-quinolin-8-yl)-benzenesulfonamideYield 100.7%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 702
Ethanol
Solvent

Procedure

In a similar fashion using route 1 general procedure 4, 4-chloro-2-nitro-N-(4-trifluoromethyl-quinolin-8-yl)-benzenesulfonamide (Intermediate 252) (365 mg, 0.84 mmol), SnCl2 (637 mg, 3.37 mmol), 6N HCl (2 drops) and EtOH (15 ml) gave the title compound (340 mg, 100%).

Sources & evidence

ORD record
ord-bd8512a7ebc64220949c8ba195a3646a
Source dataset
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09102688B2

Reaction notes

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On this pageParticipantsProcedureSources & evidenceReaction notes