Stannous Chloride → 2-Amino-N-(6-methoxyquinolin-8-yl)-benzenesulfonamide

HRID 513554Notes

Reaction equation

HRID 513554 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[C:11]([NH:13][S:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[N+:23]([O-])=O)(=[O:16])=[O:15])[CH:12]=1)[N:9]=[CH:8][CH:7]=[CH:6]2.[Sn](Cl)Cl>Cl>[NH2:23][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[S:14]([NH:13][C:11]1[CH:12]=[C:3]([O:2][CH3:1])[CH:4]=[C:5]2[C:10]=1[N:9]=[CH:8][CH:7]=[CH:6]2)(=[O:15])=[O:16]

Participants

4

Reactant 2

HCID 24479Stannous ChlorideHCID 68183106N-(6-methoxyquinolin-8-yl)-2-nitrobenzenesulfonamide2×

Product 1

HCID 681834062-Amino-N-(6-methoxyquinolin-8-yl)-benzenesulfonamideYield 68%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidCatalyst

Procedure

In a similar fashion using route 1 general procedure 4, N-(6-methoxyquinolin-8-yl)-2-nitrobenzenesulfonamide (Intermediate 152) (460 mg, 1.17 mmol), tin (II) chloride (886 mg, 4.68 mmol) and 6 N HCl (3 drops) gave the title compound (260 mg, 68%). The structure was confirmed by 1H NMR.

Sources & evidence

ORD record
ord-44545462033248cbb2236cbd161b81b3
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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