2-Methyl-5-nitrobenzene-1-sulfonamide → 5-Amino-2-methylbenzenesulfonamide

HRID 574195

Reaction equation

HRID 574195 reaction equation
[NH2:1][S:2]([C:5]1[CH:6]=[C:7]([N+:12]([O-])=O)[CH:8]=[CH:9][C:10]=1[CH3:11])(=[O:4])=[O:3]>ClCCl.CO.[Pd]>[NH2:1][S:2]([C:5]1[CH:6]=[C:7]([CH:8]=[CH:9][C:10]=1[CH3:11])[NH2:12])(=[O:3])=[O:4]

Participants

5

Reactant 1

HCID 2342822-Methyl-5-nitrobenzene-1-sulfonamide

Product 1

HCID 2355115-Amino-2-methylbenzenesulfonamide

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-aminosulfonyl-4-methylnitrobenzene in dichloromethane and methanol was added 10% Pd/C and the mixture shaken under a hydrogen atmosphere at 50 psi for 15 minutes. The mixture was filtered through diatomaceous earth and the filter cake was washed with methanol. The combined organic solvents were concentrated under reduced pressure to give crude product, which was further purified by flash column chromatography (ethyl acetate:hexanes 1:1) to give 3-aminosulfonyl-4-methylaniline, LCMS: purity: 87%; MS (m/e): 187 (MH+).

Workup

  1. filtrationThe mixture was filtered through diatomaceous earth
  2. washthe filter cake was washed with methanol
  3. concentrationThe combined organic solvents were 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-56721924960a473591934342a27241ad
Source dataset
uspto-grants-2015_05
Patent number
US09034881B2

Linked notes

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