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

HRID 2408397Notes

Reaction equation

HRID 2408397 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)([O-:3])=[O:2].Br[CH2:12][C:13]([NH2:15])=[O:14].C([O-])([O-])=O.[K+].[K+]>CC(C)=O.O>[NH2:15][C:13]([CH2:12][O:10][C:7]1[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1)=[O:14]

Participants

6

Reactant 3

HCID 9804-NitrophenolHCID 11430Potassium CarbonateHCID 696322-Bromoacetamide

Product 1

HCID 6704702-(4-nitrophenoxy)acetamideYield 81.6%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 962WaterSolvent

Procedure

4-Nitrophenol (10 g), bromoacetamide (10 g) and K2CO3 (15 g) were suspended in acetone (30 mL). The yellow solution was stirred at rt for 3 d. The reaction mixture was diluted with water and acetone was removed under reduced pressure. The light-yellow precipitate was collected by filtration, washed with water and dried to give O-aminocarbonylmethyl-4-nitrophenol (11.5 g) as a beige solid.

Workup

  1. customwas removed under reduced pressure
  2. filtrationThe light-yellow precipitate was collected by filtration
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-123b7fa90c6040049831227a440ff60a
Source dataset
uspto-grants-2014_08
Patent number
US08815848B2

Reaction notes

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