N-tert-Butyl 4-Nitrophenylsulfonamide → 4-Amino-N-(1,1-dimethylethyl)benzenesulfonamide

HRID 898749Notes

Reaction equation

HRID 898749 reaction equation
[C:1]([NH:5][S:6]([C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][CH:10]=1)(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2]>CCO.[Pd]>[NH2:15][C:12]1[CH:13]=[CH:14][C:9]([S:6]([NH:5][C:1]([CH3:4])([CH3:3])[CH3:2])(=[O:8])=[O:7])=[CH:10][CH:11]=1

Participants

4

Reactant 1

HCID 796974N-tert-Butyl 4-Nitrophenylsulfonamide

Product 1

HCID 8326274-Amino-N-(1,1-dimethylethyl)benzenesulfonamideYield 98%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of N-tert-butyl-4-nitrobenzenesulfonamide (10.0 g, 39 mmol) in EtOH (100 mL) is stirred for 48 h under a H2 atmosphere in the presence of 10% Pd/C (1.50 g). The resulting mixture is filtered and concentrated to give the desired product as a slightly-coloured solid (8.7 g, yield: 98%).

Workup

  1. filtrationThe resulting mixture is filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-7dcaed705efb4a1db0ab64b376df0991
Source dataset
uspto-grants-2008_04
Patent number
US07351836B2

Reaction notes

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