Phenol → 2-nitro-5-phenoxyaniline

HRID 373078Notes

Reaction equation

HRID 373078 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([CH:8]=1)[NH2:7].[C:12]1([OH:18])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+]>[OH-].[Na+]>[N+:9]([C:5]1[CH:4]=[CH:3][C:2]([O:18][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:8][C:6]=1[NH2:7])([O-:11])=[O:10]

Participants

5

Reactant 3

HCID 996PhenolHCID 11430Potassium CarbonateHCID 742185-Chloro-2-nitroaniline

Product 1

HCID 27601872-nitro-5-phenoxyanilineYield 48.1%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 1.09 g of 5-chloro-2-nitroaniline, 10 g of phenol and 2.0 g of anhydrous potassium carbonate was heated at 150° C for 4 days. The reaction mixture was diluted with 1N sodium hydroxide and extracted with ethyl acetate. The ethyl acetate layer was washed with 1N sodium hydroxide, water and brine in turn and dried over anhydrous sodium sulfate. After removal of the solvent, the residue was chromatographed on silica gel using chloroform to give 0.70 g of 2-nitro-5-phenoxyaniline.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with 1N sodium hydroxide, water and brine in turn
  3. dry with materialdried over anhydrous sodium sulfate
  4. customAfter removal of the solvent
  5. customthe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-3d6fbfe52e90487d98d9168bbc89ae94
Source dataset
uspto-grants-1992_11
Patent number
US05162318

Reaction notes

Loading…