Water → 1-methyl-4-nitro-1H-pyrazole

HRID 2201032Notes

Reaction equation

HRID 2201032 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][NH:7][CH:8]=1)([O-:3])=[O:2].I[CH3:10].[H-].[Na+].O>CN(C=O)C.CCOC(C)=O>[CH3:10][N:6]1[CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:8]=[N:7]1

Participants

7

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 163764-nitro-1H-pyrazoleHCID 24758Sodium hydride

Product 1

HCID 198951-methyl-4-nitro-1H-pyrazoleYield 87.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-nitro-1H-pyrazole (1.13 g, 10.0 mmol) and iodomethane (1.25 mL, 20.0 mmol) in DMF (12 mL), NaH (60% in mineral oil, 0.600 g, 15.0 mmol) was added. The mixture was stirred for 18 h. Water and EtOAc were added. The organic phase was separated, washed with water, dried over Na2SO4, concentrated in vacuo to give 1-methyl-4-nitro-1H-pyrazole as a solid (1.11 g).

Workup

  1. customThe organic phase was separated
  2. washwashed with water
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-06cf718d0d984fb8a3c6a3c5a0e03d87
Source dataset
uspto-grants-2016_06
Patent number
US09359375B2

Reaction notes

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