Nitric Acid → 3,5-Dimethyl-4-nitropyrazole

HRID 894113

Reaction equation

HRID 894113 reaction equation
[CH3:1][C:2]1[CH:6]=[C:5]([CH3:7])[NH:4][N:3]=1.[OH-].[K+].[N+:10]([O-])([OH:12])=[O:11]>S(=O)(=O)(O)O>[CH3:1][C:2]1[C:6]([N+:10]([O-:12])=[O:11])=[C:5]([CH3:7])[NH:4][N:3]=1

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 62103,5-DimethylpyrazoleHCID 14797Potassium Hydroxide

Product 1

HCID 1461723,5-Dimethyl-4-nitropyrazole

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Procedure

To a solution of 3,5-dimethylpyrazole (86.5 g, 0.90 mol) in concentrated sulfuric acid (170 ml), conc nitric acid (103 ml, d=1.423) was added with stirring and icecooling. After one hour concentrated sulfuric acid (100 ml) was added slowly with stirring resulting in a temperature rise to 70°-80° C. After stirring overnight at 30°-35° C., the mixture was poured into ice (1.5 l) and neutralized with potassium hydroxide. Extraction with methylene chloride (3×350 ml), drying of the organic phase (Na2SO4) and evaporation gave off-white crystals which were dried in vacuo at 70°. Yield 106.2 g=83.6%, m.p. 125°.

Workup

  1. stirringwith stirring
  2. customresulting in a temperature rise to 70°-80° C
  3. stirringAfter stirring overnight at 30°-35° C.
  4. extractionExtraction with methylene chloride (3×350 ml)
  5. dry with materialdrying of the organic phase (Na2SO4) and evaporation
  6. customgave off-white crystals which
  7. customwere dried in vacuo at 70°

Sources & evidence

ORD record
ord-44699a97bb514e5aa7c7f81c8017bdc3
Source dataset
uspto-grants-1981_08
Patent number
US04282361

Linked notes

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