Methyl iodide → 1,3-Dimethyl-4-nitro-1H-pyrazole

HRID 1478071Notes

Reaction equation

HRID 1478071 reaction equation
[CH3:1][C:2]1[C:6]([N+:7]([O-:9])=[O:8])=[CH:5][NH:4][N:3]=1.CI.[C:12]([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH3:12][N:4]1[CH:5]=[C:6]([N+:7]([O-:9])=[O:8])[C:2]([CH3:1])=[N:3]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178434564HCID 178434564, compound

Product 1

HCID 7028921,3-Dimethyl-4-nitro-1H-pyrazoleYield 179.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 3-methyl-4-nitro-1H-pyrazole (5.02 g, 39.5 mmol) in DMF (80 mL) were added CH3I (10.01 mg, 70.52 mmol) and K2CO3 (9.97 g). The mixture was stirred at 60° C. for 2 h, quenched with water (100 mL), and extracted with EtOAc (250 mL×3). The combined organic phases were washed with brine (100 mL), dried over anhydrous Na2SO4, filtered and concentrated in vacuo to give the title compound as brown oil (10.01 g, 89.79%).

Workup

  1. customquenched with water (100 mL)
  2. extractionextracted with EtOAc (250 mL×3)
  3. washThe combined organic phases were washed with brine (100 mL)
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-102d0bbea2124808976c10b40d854b74
Source dataset
uspto-grants-2016_08
Patent number
US09403801B2

Reaction notes

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