3-Methanesulfonyl-5-nitrobenzoic acid → 3-Amino-5-(methanesulfonyl)benzoic acid

HRID 1373103Notes

Reaction equation

HRID 1373103 reaction equation
[CH3:1][S:2]([C:5]1[CH:6]=[C:7]([CH:11]=[C:12]([N+:14]([O-])=O)[CH:13]=1)[C:8]([OH:10])=[O:9])(=[O:4])=[O:3]>CO.[Ni]>[NH2:14][C:12]1[CH:11]=[C:7]([CH:6]=[C:5]([S:2]([CH3:1])(=[O:4])=[O:3])[CH:13]=1)[C:8]([OH:10])=[O:9]

Participants

4

Reactant 1

HCID 223974393-Methanesulfonyl-5-nitrobenzoic acid

Product 1

HCID 189525063-Amino-5-(methanesulfonyl)benzoic acidYield 90.7%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

3-Methylsulfonyl-5-nitrobenzoic acid (D11) (7.5 g) was dissolved in methanol (250 ml) and Raney nickel was added. The mixture was stirred under hydrogen at atmospheric pressure and room temperature overnight. The mixture was heated to dissolve precipitated product and filtered hot. The filter cake was washed with hot MeOH and the combined filtrates were evaporated to give D12 (5.97 g) an off-white solid.

Workup

  1. temperatureThe mixture was heated
  2. dissolutionto dissolve
  3. customprecipitated product
  4. filtrationfiltered hot
  5. washThe filter cake was washed with hot MeOH
  6. customthe combined filtrates were evaporated

Sources & evidence

ORD record
ord-86499ae96bd14bfe90dbeb3bfa9691bd
Source dataset
uspto-grants-2007_01
Patent number
US07160905B2

Reaction notes

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