Methyl iodide → Methyl 1-methyl-5-nitro-1H-pyrazole-3-carboxylate

HRID 547511Notes

Reaction equation

HRID 547511 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[NH:7][N:6]=1)=[O:4].[C:13](=O)([O-])[O-].[K+].[K+].IC>CN(C)C=O>[CH3:1][O:2][C:3]([C:5]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[N:7]([CH3:13])[N:6]=1)=[O:4]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 135452337methyl 3-nitro-1H-pyrazole-5-carboxylate

Product 1

HCID 50896836Methyl 1-methyl-5-nitro-1H-pyrazole-3-carboxylateYield 58%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

500 mg (2.93 mM) of 5-nitro-1H-pyrazole-3-carboxylic acid methyl ester was dissolved in 5 ml of N,N-dimethylformamide, to which 810 mg (5.86 mM, eq) of potassium carbonate was added. Subsequently, 0.49 ml (3.22 mM) of iodomethane was added dropwise thereto at 0° C., and the resulting mixture was stirred under a nitrogen atmosphere for 1 hour. The solvent was distilled off under reduced pressure, and the resultant was extracted with ethyl acetate and brine. The organic solvent layer was dried over anhydrous sodium sulfate, filtered, and then distilled under reduced pressure. The resulting impure compound was purified by column chromatography (hexane:ethyl acetate=10:1), to obtain 314 mg (56%) of the title compound.

Workup

  1. additionwas added
  2. distillationThe solvent was distilled off under reduced pressure
  3. extractionthe resultant was extracted with ethyl acetate and brine
  4. dry with materialThe organic solvent layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. distillationdistilled under reduced pressure
  7. customThe resulting impure compound was purified by column chromatography (hexane:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-177003ed0d044a3c838ae62699424ef6
Source dataset
uspto-grants-2011_05
Patent number
US07939550B2

Reaction notes

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