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

HRID 513552Notes

Reaction equation

HRID 513552 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:5]=1[S:12]([NH:15][C:16]1[CH:17]=[CH:18][CH:19]=[C:20]2[C:25]=1[N:24]=[C:23]([CH3:26])[CH:22]=[CH:21]2)(=[O:14])=[O:13])([O-])=O.[Sn](Cl)Cl>Cl>[NH2:1][C:4]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:5]=1[S:12]([NH:15][C:16]1[CH:17]=[CH:18][CH:19]=[C:20]2[C:25]=1[N:24]=[C:23]([CH3:26])[CH:22]=[CH:21]2)(=[O:14])=[O:13]

Participants

4

Reactant 2

HCID 24479Stannous ChlorideHCID 236319492-Nitro-4-methoxy-N-(2-methyl-quinolin-8-yl)-benzenesulfonamide2×

Product 1

HCID 167599482-Amino-4-methoxy-N-(2-methyl-quinolin-8-yl)-benzenesulfonamideYield 72.8%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidCatalyst

Procedure

In the similar fashion using route 1 general procedure 4, 2-nitro-4-methoxy-N-(2-methyl-quinolin-8-yl)-benzenesulfonamide (Intermediate 150) (550 mg, 1.4 mmol), tin (II) chloride (838 mg, 4.4 mmol) and 6N HCl (2 drops) gave the title compound (350 mg, 70%).

Sources & evidence

ORD record
ord-5dd526d5e3644a9fa774717be4640a27
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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