Water → 1-isopropyl-3-methyl-4-nitro-1H-pyrazole

HRID 1045966Notes

Reaction equation

HRID 1045966 reaction equation
[CH3:1][C:2]1[C:6]([N+:7]([O-:9])=[O:8])=[CH:5][NH:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+].I[CH:17]([CH3:19])[CH3:18].O>CN(C=O)C.C(Cl)Cl>[CH:17]([N:4]1[CH:5]=[C:6]([N+:7]([O-:9])=[O:8])[C:2]([CH3:1])=[N:3]1)([CH3:19])[CH3:18]

Participants

7

Reactant 4

HCID 962WaterHCID 6362Isopropyl iodideHCID 11430Potassium CarbonateHCID 178434564HCID 178434564, compound

Product 1

HCID 252477521-isopropyl-3-methyl-4-nitro-1H-pyrazoleYield 93%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred of solution of 3-methyl-4-nitro-1H-pyrazole (0.3 g, 2.4 mmol) in DMF (10 mL) was added potassium carbonate (0.4 g, 2.9 mmol) and 2-iodopropane (0.72 mL, 7.2 mmol). The solution was stirred at room temperature for 3 hours. The reaction mixture was poured into water (50 mL) and extracted into ether (4×30 mL). The combined ethereal extracts were dried (MgSO4) and the solvent removed under vacuum to give a pale yellow oil. Several purifications were performed via column chromatography (SiO2; 200 equiv. 100% DCM) to give 1-isopropyl-3-methyl-4-nitropyrazole (11 mg, 93% isomeric purity). This was combined with another batch (110 mg, purified identically).

Workup

  1. extractionextracted into ether (4×30 mL)
  2. dry with materialThe combined ethereal extracts were dried (MgSO4)
  3. customthe solvent removed under vacuum
  4. customto give a pale yellow oil

Sources & evidence

ORD record
ord-dc6e5693f4b345a198888bb992167dfe
Source dataset
uspto-grants-2013_10
Patent number
US08569298B2

Reaction notes

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