2,3-dichloro-N-(2-fluoro-4-nitrophenyl)benzenesulfonamide → N-(4-amino-2-fluorophenyl)-2,3-dichlorobenzenesulfonamide

HRID 446339Notes

Reaction equation

HRID 446339 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[S:9]([NH:12][C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[CH:15][C:14]=1[F:22])(=[O:11])=[O:10]>[Ni].C1COCC1>[NH2:19][C:16]1[CH:17]=[CH:18][C:13]([NH:12][S:9]([C:3]2[CH:4]=[CH:5][CH:6]=[C:7]([Cl:8])[C:2]=2[Cl:1])(=[O:11])=[O:10])=[C:14]([F:22])[CH:15]=1

Participants

4

Reactant 1

HCID 669705742,3-dichloro-N-(2-fluoro-4-nitrophenyl)benzenesulfonamide

Product 1

HCID 66970470N-(4-amino-2-fluorophenyl)-2,3-dichlorobenzenesulfonamide

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2,3-dichloro-N-(2-fluoro-4-nitrophenyl)benzenesulfonamide (5.0 g, 13.7 mmol) and Raney Nickel (0.600 g) in THF (200 mL) was applied positive H2 pressure through a balloon/needle. The reaction was stirred at room temperature for 4 hours and then filtered. The mixture was concentrated and triturated with CH2Cl2 to afford N-(4-amino-2-fluorophenyl)-2,3-dichlorobenzenesulfonamide as a grey solid.

Workup

  1. filtrationfiltered
  2. concentrationThe mixture was concentrated
  3. customtriturated with CH2Cl2

Sources & evidence

ORD record
ord-b750f528c5454d33ae0c461012410605
Source dataset
uspto-grants-2013_07
Patent number
US08476434B2

Reaction notes

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