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

HRID 513573Notes

Reaction equation

HRID 513573 reaction equation
[CH3:1][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]([CH3:1])[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:10])=[O:9]

Participants

5

Reactant 2

HCID 24479Stannous ChlorideHCID 9735044-methyl-2-nitro-N-quinolin-8-ylbenzenesulfonamide2×

Product 1

HCID 167599222-Amino-4-methyl-N-quinolin-8-yl-benzenesulfonamideYield 45.5%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 702EthanolSolvent

Procedure

In a similar fashion using route 1 general procedure 4, 4-methyl-2-nitro-N-quinolin-8-yl-benzenesulfonamide (Intermediate 265) (1.3 g, 3.79 mmol), SnCl2 (2.87 g, 15.1 mmol), 6N HCl (2 drops) and EtOH (10 ml) at 85° C. for 6 h gave the title compound (540 mg, 45%) which was used in the next step without further purification.

Workup

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

Sources & evidence

ORD record
ord-a8c72cf4d35a461fa30df8db660f3a08
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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