N-(4-Mercapto-3-nitrophenyl)acetamide → N-(3-Amino-4-sulfanylphenyl)acetamide

HRID 1242041Notes

Reaction equation

HRID 1242041 reaction equation
[SH:1][C:2]1[CH:11]=[CH:10][C:5]([NH:6][C:7](=[O:9])[CH3:8])=[CH:4][C:3]=1[N+:12]([O-])=O>CO.[Pd]>[NH2:12][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:2]=1[SH:1])[NH:6][C:7](=[O:9])[CH3:8]

Participants

4

Reactant 1

HCID 21937525N-(4-Mercapto-3-nitrophenyl)acetamide

Product 1

HCID 21937579N-(3-Amino-4-sulfanylphenyl)acetamideYield 92.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A suspension of 4′-mercapto-3′-nitroacetanilide (3.0 g, 14 mmol) and 10% Pd/C (0.6 g) in MeOH (200 mL) was hydrogenated at 60 psi overnight. The catalyst was removed by filtration, and the filtrate was concentrated to give 3′-amino-4′-mercaptoacetanilide (2.5 g, 13 mmol), which was used in the next reaction immediately.

Workup

  1. customwas hydrogenated at 60 psi overnight
  2. customThe catalyst was removed by filtration
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-7c31b233135c4b49a88665d97a80fd02
Source dataset
uspto-grants-2006_10
Patent number
US07115640B2

Reaction notes

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