4-Nitrophenol → HCID 22936250, compound

HRID 387737Notes

Reaction equation

HRID 387737 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[N+:14]([C:17]1[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=1)([O-:16])=[O:15].CCN(C(C)C)C(C)C.CN1CCCC1=O>O>[N+:14]([C:17]1[CH:22]=[CH:21][C:20]([O:23][C:2]2[CH:7]=[CH:6][N:5]=[CH:4][C:3]=2[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:19][CH:18]=1)([O-:16])=[O:15]

Participants

6

Reactant 4

HCID 9804-NitrophenolHCID 13387N-methyl-2-pyrrolidoneHCID 81531DiisopropylethylamineHCID 27629164-chloro-3-phenylpyridine

Product 1

HCID 22936250HCID 22936250, compoundYield 48.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4-Chloro-3-phenylpyridine (200 mg, 1.06 mM), paranitrophenol (440 mg, 3.18 mM), Hunig's base (isoPr2EtN, diisopropylethylamine, 1 ml) and 1-methylpyrrolidone (2 ml) were stirred at 160° C. for 2 hours. Water was added, extraction was performed with ethyl acetate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel chromatography (hexane:ethyl acetate=4:1, and then 2:1) to obtain 4-(4-nitrophenoxy)-3-phenylpyridine (150 mg) as a light yellow oil.

Workup

  1. extractionextraction
  2. distillationthe solvent was distilled off under reduced pressure
  3. customThe residue was purified by silica gel chromatography (hexane

Sources & evidence

ORD record
ord-84b3d176c36e4121b27fffa659c2056a
Source dataset
uspto-grants-2013_02
Patent number
US08372981B2

Reaction notes

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