Nitric Acid → 1-(Tert-butyl)-4-nitro-1H-pyrazole

HRID 1930346Notes

Reaction equation

HRID 1930346 reaction equation
[N+:1]([O-:4])(O)=[O:2].[C:5]([N:9]1[CH:13]=[CH:12][CH:11]=[N:10]1)([CH3:8])([CH3:7])[CH3:6]>OS(O)(=O)=O>[C:5]([N:9]1[CH:13]=[C:12]([N+:1]([O-:4])=[O:2])[CH:11]=[N:10]1)([CH3:8])([CH3:7])[CH3:6]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 134698151-tert-Butyl-1H-pyrazole

Product 1

HCID 113557081-(Tert-butyl)-4-nitro-1H-pyrazoleYield 64%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
0 °C

Procedure

HNO3 (11.7 g, 185 mmol) was added dropwise to a mixture of 1-tert-butyl-1H-pyrazole (23 g, 185 mmol) in cone. H2SO4 (30 mL) at 0° C. The resulting mixture was stirred at 0° C. for 30 min and was poured onto crashed ice. The aqueous mixture was extracted with EtOAc. The combined organics were washed with brine, dried (MgSO4) and concentrated in vacuo to give 1-tert-butyl-4-nitro-1H-pyrazole (20 g, 64% yield). 1H NMR (400 MHz, DMSO-d6): δ8.85 (s, 1H), 8.23 (s, 1 H), 1.52 (s, 9 H).

Workup

  1. customat 0° C
  2. additionwas poured
  3. extractionThe aqueous mixture was extracted with EtOAc
  4. washThe combined organics were washed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0e27df84b30d480881a723dc531e70f1
Source dataset
uspto-grants-2012_05
Patent number
US08188113B2

Reaction notes

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