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

HRID 513570Notes

Reaction equation

HRID 513570 reaction equation
[F:1][C:2]1[CH:11]=[CH:10][C:9]([NH:12][S:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[N+:22]([O-])=O)(=[O:15])=[O:14])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.Cl[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:9]1[CH:10]=[CH:11][C:2]([F:1])=[C:3]2[C:8]=1[N:7]=[CH:6][CH:5]=[CH:4]2)(=[O:15])=[O:14]

Participants

5

Reactant 2

HCID 24479Stannous ChlorideHCID 68183367N-(5-Fluoro-quinolin-8-yl)-2-nitro-benzenesulfonamide2×

Product 1

HCID 681832092-Amino-N-(5-fluoro-quinolin-8-yl)-benzenesulfonamideYield 82%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 702EthanolSolvent

Procedure

In a similar fashion using route 1 general procedure 4, N-(5-Fluoro-quinolin-8-yl)-2-nitro-benzenesulfonamide (Intermediate 245) (470 mg, 1.35 mmol), SnCl2 (770 mg, 4.06 mmol), 6N HCl (6 drops) and EtOH (10 ml) for 6 h at 85° C. gave the title compound (350 mg, 82%) which was used in the next step without further purification.

Workup

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

Sources & evidence

ORD record
ord-9e6b82ead5744d98b8143826d127975d
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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