Hydrazine hydrate (1:1) → 3-Amino-4-methylsulfonylbenzoic acid

HRID 2085021Notes

Reaction equation

HRID 2085021 reaction equation
[CH3:1][S:2]([C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[CH:7][C:6]=1[N+:14]([O-])=O)(=[O:4])=[O:3].O.NN>C(O)C.CO.[Pd]>[NH2:14][C:6]1[CH:7]=[C:8]([CH:12]=[CH:13][C:5]=1[S:2]([CH3:1])(=[O:4])=[O:3])[C:9]([OH:11])=[O:10]

Participants

6

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 27238714-(Methanesulfonyl)-3-nitrobenzoic acid

Product 1

HCID 227288903-Amino-4-methylsulfonylbenzoic acidYield 70%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

4-methylsulfonyl-3-nitrobenzoic acid (0.90 g, 3.7 mmol) was dissolved in 10 mL ethanol. To it were added hydrazine monohydrate (0.46 mL, 15 mmol) and catalytic amount of 10% Pd/C. The mixture was refluxed for 1.5 hour, diluted with methanol, filtered through celite and concentrated in vacuuo to afford 3-amino-4-methylsulfonylbenzoic acid (>70%). ES-MS: (M+H)+ 216.

Workup

  1. temperatureThe mixture was refluxed for 1.5 hour
  2. filtrationfiltered through celite and
  3. concentrationconcentrated in vacuuo

Sources & evidence

ORD record
ord-842b63829015450fbf7338deaa559d57
Source dataset
uspto-grants-2004_04
Patent number
US06720317B1

Reaction notes

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