2-Fluoro-5-nitrobenzenesulfonamide → 916737-71-8

HRID 1725669Notes

Reaction equation

HRID 1725669 reaction equation
[NH2:1][S:2]([C:5]1[CH:6]=[C:7]([N+:12]([O-])=O)[CH:8]=[CH:9][C:10]=1[F:11])(=[O:4])=[O:3]>ClCCl.CO.[Pd]>[NH2:12][C:7]1[CH:8]=[CH:9][C:10]([F:11])=[C:5]([S:2]([NH2:1])(=[O:3])=[O:4])[CH:6]=1

Participants

5

Reactant 1

HCID 77303242-Fluoro-5-nitrobenzenesulfonamide

Product 1

HCID 43255387916737-71-8Yield 77.9%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-aminosulfonyl-4-fluoronitrobenzene (360 mg, 1.62 mmol) in dichloromethane (6 mL) and methanol (3 mL) was added 10% Pd/C (36 mg) and shaken under a hydrogen atmosphere at 50 psi for 15 minutes. The mixture was filtered through Celite and the cake was washed with methanol (5 mL). The combined organic solvent was concentrated under reduced pressure to give crude product, which was further purified by flash column chromatography (ethyl acetate:hexanes 1:1) to give 240 mg of 5-amino-2-fluorobenzensulfonamide as a light yellow solid. 1H NMR (DMSO-d6): δ 7.38 (s, 2H), 7.03-6.94 (m, 2H), 6.70-6.66 (m, 1H), 5.33 (s, 1H).

Workup

  1. filtrationThe mixture was filtered through Celite
  2. washthe cake was washed with methanol (5 mL)
  3. concentrationThe combined organic solvent was concentrated under reduced pressure
  4. customto give crude product, which
  5. customwas further purified by flash column chromatography (ethyl acetate:hexanes 1:1)

Sources & evidence

ORD record
ord-4079e3ad79bc40f9a1c582da291d9c62
Source dataset
uspto-grants-2009_02
Patent number
US07491732B2

Reaction notes

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