Stannous Chloride → 2-Amino-N-(5-chloro-quinolin-8-yl)-benzenesulfonamide

HRID 513574Notes

Reaction equation

HRID 513574 reaction equation
Cl[C:2]1[C:11]2[C:6](=[C:7]([NH:12][S:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[N+:22]([O-])=O)(=[O:15])=[O:14])[CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1.[Cl:25][Sn]Cl>Cl.CCO>[NH2:22][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[S:13]([NH:12][C:7]1[CH:8]=[CH:9][C:10]([Cl:25])=[C:11]2[C:6]=1[N:5]=[CH:4][CH:3]=[CH:2]2)(=[O:15])=[O:14]

Participants

5

Reactant 2

HCID 24479Stannous ChlorideHCID 68182953N-(4-Chloro-quinolin-8-yl)-2-nitro-benzenesulfonamide2×

Product 1

HCID 681833472-Amino-N-(5-chloro-quinolin-8-yl)-benzenesulfonamideYield 68.5%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 702EthanolSolvent

Procedure

In a similar fashion using route 1 general procedure 4, N-(5-chloro-quinolin-8-yl)-2-nitro-benzenesulfonamide (Intermediate 246) (600 mg, 1.64 mmol), SnCl2 (940 mg, 4.94 mmol), 6N HCl (5-6 drops) and EtOH (12 ml) at 80° C. for 3 h, gave the title compound (375 mg, 55%) which was used in the next step without further purification.

Workup

  1. customat 80° C.
  2. customfor 3 h

Sources & evidence

ORD record
ord-1b8ae9304b1b4b9d993ca6277a043d33
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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