Methyl 3-methanesulfonyl-5-nitrobenzoate → Methyl 3-amino-5-(methylsulfonyl)benzoate

HRID 1957969Notes

Reaction equation

HRID 1957969 reaction equation
[CH3:1][O:2][C:3](=[O:17])[C:4]1[CH:9]=[C:8]([N+:10]([O-])=O)[CH:7]=[C:6]([S:13]([CH3:16])(=[O:15])=[O:14])[CH:5]=1>CO.[Pd]>[CH3:1][O:2][C:3](=[O:17])[C:4]1[CH:5]=[C:6]([S:13]([CH3:16])(=[O:15])=[O:14])[CH:7]=[C:8]([NH2:10])[CH:9]=1

Participants

4

Reactant 1

HCID 43449009Methyl 3-methanesulfonyl-5-nitrobenzoate

Product 1

HCID 18945412Methyl 3-amino-5-(methylsulfonyl)benzoate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

3-(Methylsulfonyl)-5-nitro-benzoic acid methyl ester (32 g; 0.12 mol) was dissolved in methanol (300 ml), 4 g Pd/C (5%) were added and the mixture was hydrogenated at 5 bar. The mixture was filtered and the filtrate concentrated. 26 g (0.11 mmol; 94% yield) were obtained as a colorless solid.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate concentrated
  3. custom26 g (0.11 mmol; 94% yield) were obtained as a colorless solid

Sources & evidence

ORD record
ord-99cedfc178e748d39562ad3c0b31bca9
Source dataset
uspto-grants-2013_04
Patent number
US08410100B2

Reaction notes

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