Stannous Chloride → 2-Amino-N-(5-methoxy-quinolin-8-yl)-4-trifluoromethyl-benzenesulfonamide

HRID 513820Notes

Reaction equation

HRID 513820 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]([NH:13][S:14]([C:17]2[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][C:18]=2[N+:27]([O-])=O)(=[O:16])=[O:15])=[C:9]2[C:4]=1[CH:5]=[CH:6][CH:7]=[N:8]2.Cl[Sn]Cl>Cl.CCO>[NH2:27][C:18]1[CH:19]=[C:20]([C:23]([F:25])([F:24])[F:26])[CH:21]=[CH:22][C:17]=1[S:14]([NH:13][C:10]1[CH:11]=[CH:12][C:3]([O:2][CH3:1])=[C:4]2[C:9]=1[N:8]=[CH:7][CH:6]=[CH:5]2)(=[O:15])=[O:16]

Participants

5

Reactant 2

HCID 24479Stannous ChlorideHCID 68183320N-(5-Methoxy-quinolin-8-yl)-2-nitro-4-trifluoromethyl-benzenesulfonamide

Product 1

HCID 681833652-Amino-N-(5-methoxy-quinolin-8-yl)-4-trifluoromethyl-benzenesulfonamideYield 94.6%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 702EthanolSolvent

Procedure

In a similar fashion using route 2 general procedure 4 N-(5-methoxy-quinolin-8-yl)-2-nitro-4-trifluoromethyl-benzenesulfonamide 587 (500 mg, 1.17 mmol), SnCl2 (0.9 g, 4.6 mmol), 6N HCl (2 drops) and EtOH (10 ml) at 85° C. for 48 h gave the title compound (440 mg, 92%) which was used in the next step without further purification.

Workup

  1. customat 85° C.
  2. customfor 48 h

Sources & evidence

ORD record
ord-1eb25f39b6264b609616a70af4d0b586
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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