8-Hydroxyquinoline → 4-nitro-1-phenyl-1H-pyrazole

HRID 1846738Notes

Reaction equation

HRID 1846738 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][NH:7][CH:8]=1)([O-:3])=[O:2].I[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.OC1C=CC=C2C=1N=CC=C2.C([O-])([O-])=O.[K+].[K+]>CS(C)=O.[Cu]I.O>[N+:1]([C:4]1[CH:5]=[N:6][N:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:8]=1)([O-:3])=[O:2]

Participants

8

Reactant 4

HCID 19238-HydroxyquinolineHCID 11430Potassium CarbonateHCID 11575IodobenzeneHCID 163764-nitro-1H-pyrazole

Product 1

HCID 27558944-nitro-1-phenyl-1H-pyrazoleYield 100.8%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

A mixture of 4-nitropyrazole (270 mg, 2.38 mmol), iodobenzene (485 mg, 2.38 mmol), 8-hydroxyquinoline (60 mg, 0.41 mmol) and K2CO3 (600 mg, 4.34 mmol) in DMSO (3 mL) was degassed with argon before being charged with CuI (45 mg, 0.23 mmol). The mixture in a sealed tube was heated at 130 C for 20 h. Water was added to induce precipitation. The precipitate was collected to give 4-nitro-1-phenyl-1H-pyrazole (454 mg).

Workup

  1. customwas degassed with argon
  2. temperatureThe mixture in a sealed tube was heated at 130 C for 20 h
  3. customprecipitation
  4. customThe precipitate was collected

Sources & evidence

ORD record
ord-d85945728a9e4f5a9eec86315630060d
Source dataset
uspto-grants-2015_02
Patent number
US08952027B2

Reaction notes

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