Potassium Iodide → HCID 15887602, compound

HRID 1275685Notes

Reaction equation

HRID 1275685 reaction equation
[NH2:1][C:2]1[CH:15]=[CH:14][CH:13]=[CH:12][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1.[N+:16]([C:19]1[CH:20]=[C:21]([CH:24]=[CH:25][CH:26]=1)[CH2:22]Cl)([O-:18])=[O:17].[I-].[K+].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O>[N+:16]([C:19]1[CH:20]=[C:21]([CH:24]=[CH:25][CH:26]=1)[CH2:22][O:11][C:8]1[CH:7]=[CH:6][C:5]([O:4][C:3]2[CH:12]=[CH:13][CH:14]=[CH:15][C:2]=2[NH2:1])=[CH:10][CH:9]=1)([O-:18])=[O:17]

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 12078alpha-Chloro-m-nitrotolueneHCID 22117681HCID 22117681, compound

Product 1

HCID 15887602HCID 15887602, compoundYield 45.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 4-(2-aminophenoxy)phenol (0.85 g, 4.2 mmol) in N,N-dimethylformamide (20 ml) were added 3-nitrobenzyl chloride (0.87 g, 5.1 mmol), potassium iodide (0.70 g, 4.2 mmol) and potassium carbonate (0.88 g, 6.4 mmol), followed by stirring at 50° C. for 3 hours. The reaction solution was poured into water and extracted with ethyl acetate, and the organic layer was washed with water and a saturated aqueous sodium chloride solution. After drying, the solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent; chloroform) to give 2-[4-(3-nitrobenzyloxy)phenoxy]aniline (0.64 g)

Workup

  1. extractionextracted with ethyl acetate
  2. washthe organic layer was washed with water
  3. customAfter drying
  4. customthe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (eluent; chloroform)

Sources & evidence

ORD record
ord-f97b588a18aa42db834772505ee7d243
Source dataset
uspto-grants-2000_12
Patent number
US06162832

Reaction notes

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