Pyridine → 4-nitro-1-phenyl-1H-pyrazole

HRID 1968546Notes

Reaction equation

HRID 1968546 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][NH:7][CH:8]=1)([O-:3])=[O:2].[C:9]1(B(O)O)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.N1C=CC=CC=1>ClCCl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[N+:1]([C:4]1[CH:5]=[N:6][N:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:8]=1)([O-:3])=[O:2]

Participants

6

Reactant 3

HCID 1049PyridineHCID 163764-nitro-1H-pyrazoleHCID 66827Phenylboronic Acid

Product 1

HCID 27558944-nitro-1-phenyl-1H-pyrazole

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

4-Nitro-1H-pyrazole (1 g, 8.84 mmol), phenylboronic acid (2.223 g, 17.69 mmol), copper (II) acetate (2.409 g, 13.27 mmol) and pyridine (2.86 ml, 35.4 mmol) were combined in dichloromethane (40 ml) and the mixture stirred at ambient temperature open to the air with a drying tube. The mixture was filtered through a diatomaceous earth pad washing with dichloromethane; and the filtrate washed with water and brine, dried over MgSO4, filtered and concentrated to give the title compound.

Workup

  1. filtrationThe mixture was filtered through a diatomaceous earth pad
  2. washwashing with dichloromethane
  3. washand the filtrate washed with water and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-276d9053ee0a41ceb3c4cbabd50e2ffa
Source dataset
uspto-grants-2013_04
Patent number
US08426408B2

Reaction notes

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