Pyridine → methyl 4-nitro-1-phenyl-1H-pyrazole-3-carboxylate

HRID 902203Notes

Reaction equation

HRID 902203 reaction equation
[N+:1]([C:4]1[C:5]([C:9]([O-:11])=[O:10])=[N:6][NH:7][CH:8]=1)([O-:3])=[O:2].[C:12]1(OB(O)O)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.N1C=CC=C[CH:23]=1>C([O-])(=O)C.[Cu+2].C([O-])(=O)C.[Cl-]>[N+:1]([C:4]1[C:5]([C:9]([O:11][CH3:23])=[O:10])=[N:6][N:7]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:8]=1)([O-:3])=[O:2]

Participants

6

Reactant 3

HCID 1049PyridineHCID 78412Phenyl dihydrogen orthoborateHCID 178524955HCID 178524955, compound

Product 1

HCID 23084897methyl 4-nitro-1-phenyl-1H-pyrazole-3-carboxylateYield 83.8%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 312ChlorideSolvent

Procedure

To a solution of 4-nitro-1H-pyrazole-3-carboxylate (1.0 g, 5.84 mmol) inmethylene chloride (20 mL) were added phenylboric acid (1.43 g, 11.7 mmol), copper(II) acetate (1.60 g, 8.76 mmol) and pyridine (2 mL, 23.4 mmol), and the mixture was stirred overnight at room temperature under an air atmosphere. After removal of the insolubles by filtration, the filtrate was washed with water (twice) and saturated brine, dried over anhydrous magnesium sulfate and concentrated in vacuo to obtain the title compound (1.21 g, 83.5%).

Workup

  1. customAfter removal of the insolubles
  2. filtrationby filtration
  3. washthe filtrate was washed with water (twice) and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d2db3cb206df4545b8f69fad5ff6b560
Source dataset
uspto-grants-2008_04
Patent number
US07365079B2

Reaction notes

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