Stannous chloride dihydrate → 2-Amino-4,5-dimethyl-N-quinolin-8-yl-benzenesulfonamide

HRID 513548Notes

Reaction equation

HRID 513548 reaction equation
[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([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:4]([N+:23]([O-])=O)[CH:3]=1.O.O.[Sn](Cl)Cl>>[NH2:23][C:4]1[CH:3]=[C:2]([CH3:1])[C:7]([CH3:8])=[CH:6][C:5]=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

3

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 681834634,5-dimethyl-2-nitro-N-quinolin-8-yl-benzenesulfonamide2×

Product 1

HCID 681833912-Amino-4,5-dimethyl-N-quinolin-8-yl-benzenesulfonamideYield 66%

Procedure

In a similar fashion using route 15 general procedure 29, 4,5-dimethyl-2-nitro-N-quinolin-8-yl-benzenesulfonamide (Intermediate 147) (0.52 g, 1.45 mmol) and tin (II) chloride dihydrate (1.37 g, 7.26 mmol) gave the title compound (0.31 g, 66%).

Sources & evidence

ORD record
ord-40a2673145544a35992358d1fcf3b5ad
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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