5-(Methylsulfanyl)-2-nitrobenzoic acid → 2-Amino-5-(methylsulfanyl)benzoic acid

HRID 443826Notes

Reaction equation

HRID 443826 reaction equation
[CH3:1][S:2][C:3]1[CH:4]=[CH:5][C:6]([N+:12]([O-])=O)=[C:7]([CH:11]=1)[C:8]([OH:10])=[O:9].[H][H]>[Ni].CO>[CH3:1][S:2][C:3]1[CH:4]=[CH:5][C:6]([NH2:12])=[C:7]([CH:11]=1)[C:8]([OH:10])=[O:9]

Participants

5

Reactant 2

HCID 89345765-(Methylsulfanyl)-2-nitrobenzoic acidHCID 178418361HCID 178418361, compound2×

Product 1

HCID 127132522-Amino-5-(methylsulfanyl)benzoic acid

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A mixture of 5-methylthio-2-nitrobenzoic acid (25.4 g; 0.119 mole), methanol (200 ml) and Raney nickel (2 g) is shaken in an atmosphere of hydrogen at 50 lb pressure when theoretical amount of hydrogen is absorbed. The catalyst is filtered off and the filtrate evaporated to dryness. The residue is recrystallized from etheriso-Pr2O. Yield 7.6 g; mp 145°-150°.

Workup

  1. customis absorbed
  2. filtrationThe catalyst is filtered off
  3. customthe filtrate evaporated to dryness
  4. customThe residue is recrystallized from etheriso-Pr2O

Sources & evidence

ORD record
ord-b25cfef8cded444f874966915cfbe930
Source dataset
uspto-grants-1981_04
Patent number
US04261996

Reaction notes

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