4-Nitrophenol → 2-(4-nitrophenoxy)acetamide

HRID 357729Notes

Reaction equation

HRID 357729 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)([O-:3])=[O:2].I[CH2:12][C:13]([NH2:15])=[O:14].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:12][C:13]([NH2:15])=[O:14])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 9804-NitrophenolHCID 3727IodoacetamideHCID 11430Potassium Carbonate

Product 1

HCID 6704702-(4-nitrophenoxy)acetamideYield 74.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 4-nitrophenol (7.5 g), iodoacetamide (10 g), potassium carbonate (7.5 g) and dimethylformamide (50 ml) was stirred at 50° C. for 15 hours. The mixture was poured into ice-water, and extracted with ethyl acetate. The extract was washed with water and saturated aqueous sodium chloride, and dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was recrystallized from acetone-diisopropyl ether to give the desired compound (7.9 g) as colorless crystals.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water and saturated aqueous sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was recrystallized from acetone-diisopropyl ether

Sources & evidence

ORD record
ord-a92164c3c472481099d0c95db75561ae
Source dataset
uspto-grants-1998_11
Patent number
US05840917

Reaction notes

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