methyl 2-(N-tert-butylsulfamoyl)-4-nitrobenzoate → methyl 4-amino-2-(N-tert-butylsulfamoyl)benzoate

HRID 2399585Notes

Reaction equation

HRID 2399585 reaction equation
[C:1]([NH:5][S:6]([C:9]1[CH:14]=[C:13]([N+:15]([O-])=O)[CH:12]=[CH:11][C:10]=1[C:18]([O:20][CH3:21])=[O:19])(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H]>CO.[Pd]>[C:1]([NH:5][S:6]([C:9]1[CH:14]=[C:13]([NH2:15])[CH:12]=[CH:11][C:10]=1[C:18]([O:20][CH3:21])=[O:19])(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 15240542methyl 2-(N-tert-butylsulfamoyl)-4-nitrobenzoateHCID 178418361HCID 178418361, compound

Product 1

HCID 10946074methyl 4-amino-2-(N-tert-butylsulfamoyl)benzoate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

25.08 g (0.079 mol) of N-tert-butyl-2-methoxycarbonyl-5-nitrobenzenesulfonamide are dissolved in 1000 ml of MeOH. 0.50 g of Pd-C (10%) is added and the mixture is shaken under a hydrogen atmosphere (1 atm) until the uptake of hydrogen has finished. The catalyst is separated off and the solvent is removed by distillation. The residue is induced to crystallize by stirring with a little ethyl acetate. The resulting N-tert-butyl-5-amino-2-methoxycarbonylbenzenesulfonamide (18.3 g; 80.9% of theory) melts at 193° C.

Workup

  1. customThe catalyst is separated off
  2. customthe solvent is removed by distillation
  3. customto crystallize

Sources & evidence

ORD record
ord-93472d26c82947fca04307aa781dce04
Source dataset
uspto-grants-1995_09
Patent number
US05449812

Reaction notes

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