5-[4-(Methylsulfonyl)phenyl]-2-nitrothiophene-3-carboxamide → 2-Amino-5-[4-(methylsulfonyl)phenyl]thiophene-3-carboxamide

HRID 385715Notes

Reaction equation

HRID 385715 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[S:15][C:14]([N+:16]([O-])=O)=[C:13]([C:19]([NH2:21])=[O:20])[CH:12]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3]>CO.[Pt]>[NH2:16][C:14]1[S:15][C:11]([C:8]2[CH:7]=[CH:6][C:5]([S:2]([CH3:1])(=[O:4])=[O:3])=[CH:10][CH:9]=2)=[CH:12][C:13]=1[C:19]([NH2:21])=[O:20]

Participants

4

Reactant 1

HCID 595257655-[4-(Methylsulfonyl)phenyl]-2-nitrothiophene-3-carboxamide

Product 1

HCID 582564812-Amino-5-[4-(methylsulfonyl)phenyl]thiophene-3-carboxamide

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 887MethanolSolvent

Procedure

Nitro reduction, Method A: 5-[4-(Methylsulfonyl)phenyl]-2-nitrothiophene-3-carboxamide (0.96 g, 2.94 mmol) and Pt/C, doped with V (0.191 g, 0.029 mmol) were stirred in MeOH (60 mL) at room temperature under a balloon of H2 for 90 minutes. The catalyst was removed by filtering through Celite, which was subsequently washed with DMF. The solvent was removed in vacuo and the residue triturated in EtOH to give the title compound as a dark brown solid.

Workup

  1. customThe catalyst was removed
  2. filtrationby filtering through Celite, which
  3. washwas subsequently washed with DMF
  4. customThe solvent was removed in vacuo
  5. customthe residue triturated in EtOH

Sources & evidence

ORD record
ord-6d60e84ed0044eb395e6fdf29b43a93b
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Reaction notes

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