3-Fluoro-4-nitrobenzene-1-sulfonamide → 4-Amino-3-fluorobenzene-1-sulfonamide

HRID 1396039Notes

Reaction equation

HRID 1396039 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([S:11]([NH2:14])(=[O:13])=[O:12])[CH:5]=[CH:6][C:7]=1[N+:8]([O-])=O>CO.[Pd]>[NH2:8][C:7]1[CH:6]=[CH:5][C:4]([S:11]([NH2:14])(=[O:12])=[O:13])=[CH:3][C:2]=1[F:1]

Participants

4

Reactant 1

HCID 581586953-Fluoro-4-nitrobenzene-1-sulfonamide

Product 1

HCID 46874724-Amino-3-fluorobenzene-1-sulfonamideYield 74%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 1.00 g 3-fluoro-4-nitro-benzenesulfonamide in 10 mL MeOH was added 10 mol % of palladium on carbon. The mixture was hydrogenated for 30 minutes at a H2 pressure of 50 psi. After filtration over Hyflo, concentration in vacuo yielded 630 mg (74%) of a dark-brown oil. 1H NMR (400 MHz, DMSO-d6) δ 6.83 (t, J=8.43 Hz, 1H), 7.42 (dd, J=8.28, 1.96 Hz, 1H), 7.47 (dd, J=10.99, 1.96 Hz, 1H) [NH2's invisible].

Workup

  1. filtrationAfter filtration
  2. concentrationover Hyflo, concentration in vacuo

Sources & evidence

ORD record
ord-437f7173c91a45d68c948a95d5733824
Source dataset
uspto-grants-2014_12
Patent number
US08901108B2

Reaction notes

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