N-methyl-3-(4-nitrophenoxy)benzamide → 3-(4-Aminophenoxy)-N-methylbenzamide

HRID 598448

Reaction equation

HRID 598448 reaction equation
[CH3:1][NH:2][C:3]([C:5]1[CH:6]=[C:7]([CH:18]=[CH:19][CH:20]=1)[O:8][C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][CH:10]=1)=[O:4]>CCOC(C)=O.[Pd]>[CH3:1][NH:2][C:3]([C:5]1[CH:6]=[C:7]([CH:18]=[CH:19][CH:20]=1)[O:8][C:9]1[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][CH:10]=1)=[O:4]

Participants

4

Reactant 1

HCID 23614569N-methyl-3-(4-nitrophenoxy)benzamide

Product 1

HCID 236145703-(4-Aminophenoxy)-N-methylbenzamideYield 56.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A slurry of 4-(3-(N-methylcarbamoyl)phenoxy)-1-nitrobenzene (1.89 g, 6.95 mmol) and 5% Pd/C (0.24 g) in EtOAc (20 mL) was stirred under an H2 atm (balloon) overnight. The resulting mixture was filtered through a pad of Celite® and concentrated under reduced pressure. The residue was purified by column chromatography (5% MeOH/95% CH2Cl2). The resulting oil solidified under vacuum overnight to give 4-(3-(N-methylcarbamoyl)phenoxy)aniline as a yellow solid (0.95 g, 56%).

Workup

  1. filtrationThe resulting mixture was filtered through a pad of Celite®
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was purified by column chromatography (5% MeOH/95% CH2Cl2)
  4. customsolidified under vacuum overnight

Sources & evidence

ORD record
ord-0d096a36eb0c44f6b7fce3e800d192fd
Source dataset
uspto-grants-2011_03
Patent number
US07897623B2

Linked notes

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