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

HRID 1880314Notes

Reaction equation

HRID 1880314 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-144a2bf57523423d934f3d09c291062b
Source dataset
uspto-grants-2012_11
Patent number
US08318755B2

Reaction notes

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