N-(2-nitrophenyl)methanesulfonamide → N-(2-aminophenyl)methanesulfonamide

HRID 629197Notes

Reaction equation

HRID 629197 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][S:11]([CH3:14])(=[O:13])=[O:12])([O-])=O>CO.[Pd]>[NH2:1][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][S:11]([CH3:14])(=[O:13])=[O:12]

Participants

4

Reactant 1

HCID 296454N-(2-nitrophenyl)methanesulfonamide

Product 1

HCID 241357N-(2-aminophenyl)methanesulfonamideYield 87.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of N-(2-nitrophenyl)methanesulfonamide (800 mg, 3.70 mmol) in methanol (20 mL) was added palladium on carbon (10% by weight, 394 mg, 0.37 mmol). The vessel was purged with hydrogen and then stirred for 4 hours under 1 atm of hydrogen. The reaction was filtered, concentrated and purified by chromatography to provide N-(2-aminophenyl)methanesulfonamide (600 mg, 87% yield). 1H NMR (300 MHz, DMSO-d6) δ 8.67 (bs, 1H), 7.05 (dd, J=7.8, 1.5 Hz, 1H), 6.98 (m, 1H), 6.73 (dd, J=7.8, 1.5 Hz, 1H), 6.54 (m, 1H), 5.11 (bs, 2H), 2.90 (s, 3H).

Workup

  1. customThe vessel was purged with hydrogen
  2. filtrationThe reaction was filtered
  3. concentrationconcentrated
  4. custompurified by chromatography

Sources & evidence

ORD record
ord-217cd7d0099d438fac43a090e8be2b1e
Source dataset
uspto-grants-2016_04
Patent number
US09315494B2

Reaction notes

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