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

HRID 513571Notes

Reaction equation

HRID 513571 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([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])=[C:4]([N+:22]([O-])=O)[CH:3]=1.Cl[Sn]Cl>Cl.CCO>[NH2:22][C:4]1[CH:3]=[C:2]([Cl:1])[CH:7]=[CH:6][C:5]=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:9])=[O:10]

Participants

5

Reactant 2

HCID 24479Stannous ChlorideHCID 236319584-Chloro-2-nitro-N-quinolin-8-yl-benzenesulfonamide2×

Product 1

HCID 167599552-Amino-4-chloro-N-quinolin-8-yl-benzenesulfonamideYield 59.1%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 702EthanolSolvent

Procedure

In a similar fashion using route 1 general procedure 4, 4-chloro-2-nitro-N-quinolin-8-yl-benzenesulfonamide (Intermediate 263) (280 mg, 0.77 mmol), SnCl2 (383 mg, 3.08 mmol), 6N HCl (2 drops) and EtOH (4 ml) for 6 h at 85° C. gave the title compound (152 mg, 59%) after purification by column chromatography with DCM/MeOH (97:3) as the eluent.

Workup

  1. customfor 6 h
  2. customat 85° C.

Sources & evidence

ORD record
ord-5422d8bb7d9242d9b9e9929b24ec2d1b
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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