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

HRID 1417987Notes

Reaction equation

HRID 1417987 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+]>>[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])[NH2:15]

Participants

4

Reactant 3

HCID 9804-NitrophenolHCID 3727IodoacetamideHCID 11430Potassium Carbonate

Product 1

HCID 6704702-(4-nitrophenoxy)acetamideYield 33.5%

Procedure

A mixture of 4-nitrophenol (2.8 g), iodoacetamide (3.72 g) and potassium carbonate (2.8 g) in DHF (50 ml) was reacted. The product so obtained was recrystallised from a mixture of ethyl acetate and hexane to give 4-(carbamoylmethoxy)nitrobenzene (1.32 g), m.p. 153°-156° C. The product so obtained was dissolved in ethyl acetate and hydrogenated in the presence of a 10% Pd/C catalyst. The product so obtained was recrystallised from a mixture of ethyl acetate and hexane to give 4-(carbamoylmethoxy)aniline (0.58 g), m.p. 125°-127° C.;

Workup

  1. customwas reacted
  2. customThe product so obtained
  3. customwas recrystallised from a mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-140d88a94d8a48c8ad03622ee79e117c
Source dataset
uspto-grants-1999_03
Patent number
US05880130

Reaction notes

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