4-fluoro-N-methyl-3-nitrobenzenesulfonamide → 3-Amino-4-fluoro-N-methyl-benzenesulfonamide

HRID 536045Notes

Reaction equation

HRID 536045 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH3:12])(=[O:10])=[O:9])=[CH:4][C:3]=1[N+:13]([O-])=O>C1COCC1.[Pd]>[NH2:13][C:3]1[CH:4]=[C:5]([S:8]([NH:11][CH3:12])(=[O:9])=[O:10])[CH:6]=[CH:7][C:2]=1[F:1]

Participants

4

Reactant 1

HCID 84680854-fluoro-N-methyl-3-nitrobenzenesulfonamide

Product 1

HCID 242707693-Amino-4-fluoro-N-methyl-benzenesulfonamideYield 89.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a mixture of 4-fluoro-N-methyl-3-nitrobenzenesulfonamide (1.6 g, 6.83 mmol) in THF (50 mL) under nitrogen, Pd/C (0.600 g) was added. The flask was then evacuated and recharged with hydrogen. The resulting mixture was allowed to stir under a hydrogen atmosphere overnight at 50° C. The mixture was then filtered and concentrated to afford 3-amino-4-fluoro-N-methylbenzenesulfonamide (1.25 g, 89%) as an off-white solid. 1H NMR (400 MHz, DMSO-d6) δ 7.26 (q, J=4.85 Hz, 1H), 7.13-7.22 (m, 2H), 6.90 (ddd, J=2.38, 4.27, 8.41 Hz, 1H), 5.63 (s, 2H), 2.40 (d, J=5.02 Hz, 3H); MS (m/z) 205.1 (M+H+)

Workup

  1. customThe flask was then evacuated
  2. filtrationThe mixture was then filtered
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-6b8bdaf1ef3546678402af6ba1a4fca3
Source dataset
uspto-grants-2014_10
Patent number
US08859571B2

Reaction notes

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