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

HRID 2122011Notes

Reaction equation

HRID 2122011 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-6d4405f9329a4a94b74332ea2f037579
Source dataset
uspto-grants-2004_02
Patent number
US06696473B2

Reaction notes

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