Stannous chloride dihydrate → 2-Amino-N-quinolin-8-yl-benzenesulfonamide

HRID 513545Notes

Reaction equation

HRID 513545 reaction equation
O.O.[Sn](Cl)Cl.[N+:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[S:15]([NH:18][C:19]1[CH:20]=[CH:21][CH:22]=[C:23]2[C:28]=1[N:27]=[CH:26][CH:25]=[CH:24]2)(=[O:17])=[O:16])([O-])=O>CCO>[NH2:6][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[S:15]([NH:18][C:19]1[CH:20]=[CH:21][CH:22]=[C:23]2[C:28]=1[N:27]=[CH:26][CH:25]=[CH:24]2)(=[O:17])=[O:16]

Participants

4

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 7394492-nitro-N-(quinolin-8-yl)benzenesulfonamide2×

Product 1

HCID 10701592-Amino-N-quinolin-8-yl-benzenesulfonamideYield 100.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Tin (II) chloride dihydrate (4.11 g, 18.2 mmol) was added to a solution of 2-nitro-N-quinolin-8-yl-benzenesulfonamide (Example Compound 6) (2.0 g, 6.07 mmol) in EtOH (50 ml) and the mixture was heated under reflux for 2 h. After cooling, the mixture was concentrated in vacuo. The crude residue was dissolved in EtOAc (40 ml) and cooled in an ice bath, the mixture was basified with aqueous ammonia. The resulting white precipitate was collected by filtration, washed with EtOAc and discarded. The organic combined organic filtrates were washed with brine, dried (Na2SO4) and concentrated in vacuo to give the title compound (1.82 g, 53%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 2 h
  3. temperatureAfter cooling
  4. concentrationthe mixture was concentrated in vacuo
  5. dissolutionThe crude residue was dissolved in EtOAc (40 ml)
  6. temperaturecooled in an ice bath
  7. filtrationThe resulting white precipitate was collected by filtration
  8. washwashed with EtOAc
  9. washThe organic combined organic filtrates were washed with brine
  10. dry with materialdried (Na2SO4)
  11. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a3b0524498184d1fac8cfc3fb199a40a
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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