N-Methyl-N-(3-nitrophenyl)acetamide → N-(3-aminophenyl)-N-methylacetamide

HRID 2086773Notes

Reaction equation

HRID 2086773 reaction equation
[CH3:1][N:2]([C:12](=[O:14])[CH3:13])[C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([N+:9]([O-])=O)[CH:4]=1>CO.O1CCOCC1.[C].[Pd]>[NH2:9][C:5]1[CH:4]=[C:3]([CH:8]=[CH:7][CH:6]=1)[N:2]([CH3:1])[C:12](=[O:14])[CH3:13]

Participants

5

Reactant 1

HCID 676602N-Methyl-N-(3-nitrophenyl)acetamide

Product 1

HCID 10607115N-(3-aminophenyl)-N-methylacetamideYield 93.6%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of N-methyl-3′-nitroacetanilide (5.13 g) and 10% palladium carbon (0.6 g) in methanol (50 ml) and 1,4-dioxane (50 ml) and stirred under hydrogen (3 atm) at room temperature for 2 hours. The catalyst was removed by filtration and the solvent was evaporated. The resultant solid was collected and washed with isopropyl ether to give 3′-amino-N-methylacetanilide (4.06 g).

Workup

  1. customThe catalyst was removed by filtration
  2. customthe solvent was evaporated
  3. customThe resultant solid was collected
  4. washwashed with isopropyl ether

Sources & evidence

ORD record
ord-a4591cbfeff842939090836940f4aaca
Source dataset
uspto-grants-2004_04
Patent number
US06727245B2

Reaction notes

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