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

HRID 513549Notes

Reaction equation

HRID 513549 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([NH:12][C:13]2[CH:14]=[CH:15][CH:16]=[C:17]3[C:22]=2[N:21]=[CH:20][CH:19]=[CH:18]3)(=[O:11])=[O:10])=[C:5]([N+:23]([O-])=O)[CH:4]=1.[Sn](Cl)Cl>Cl>[NH2:23][C:5]1[CH:4]=[C:3]([O:2][CH3:1])[CH:8]=[CH:7][C:6]=1[S:9]([NH:12][C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[C:22]=1[N:21]=[CH:20][CH:19]=[CH:18]2)(=[O:11])=[O:10]

Participants

4

Reactant 2

HCID 24479Stannous ChlorideHCID 167595474-Methoxy-2-nitro-N-quinolin-8-yl-benzenesulfonamide2×

Product 1

HCID 167595172-Amino-4-methoxy-N-quinolin-8-yl-benzenesulfonamideYield 56.9%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidCatalyst

Procedure

In the similar fashion using route 1 general procedure 4, 4-methoxy-2-nitro-N-quinolin-8-yl-benzenesulfonamide (Example Compound 34) (600 mg, 1.6 mmol), tin (II) chloride (950 mg, 5.0 mmol) and 6N HCl (2 drops) gave the title compound (300 mg, 54%).

Sources & evidence

ORD record
ord-162ba09d5d6c49eb97df3603f318a884
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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