Stannous Chloride → HCID 68183321, compound

HRID 513575Notes

Reaction equation

HRID 513575 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([N+:22]([O-])=O)=[C:6]([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]=[CH:17]3)(=[O:10])=[O:9])[CH:7]=1.Cl[Sn]Cl>Cl.CCO>[NH2:22][C:5]1[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][C:6]=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]=[CH:17]2)(=[O:10])=[O:9]

Participants

5

Reactant 2

HCID 24479Stannous ChlorideHCID 681831575-Methyl-2-nitro-N-quinolin-8-yl-benzenesulfonamide2×

Product 1

HCID 68183321HCID 68183321, compoundYield 50.1%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 702EthanolSolvent

Procedure

In a similar fashion using route 1 general procedure 4, 5-methyl-2-nitro-N-quinolin-8-yl-benzenesulfonamide (Intermediate 266) (350 mg, 1.02 mmol), SnCl2 (773 mg, 4.08 mmol), 6N HCl (5 drops) and EtOH (5 ml), at 80° C. for 2 h gave the title compound (160 mg, 50%) after purification by column chromatography with n-hexane/EtOAc (98:2) as the eluent.

Sources & evidence

ORD record
ord-7310400fabff4a099dd7b5cd49548e92
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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