Potassium Nitrate → 1-Isopropyl-4-nitro-1H-pyrazole

HRID 1098562Notes

Reaction equation

HRID 1098562 reaction equation
[CH:1]([N:4]1[CH:8]=[CH:7][CH:6]=[N:5]1)([CH3:3])[CH3:2].[N+:9]([O-])([O-:11])=[O:10].[K+]>OS(O)(=O)=O>[CH:1]([N:4]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[N:5]1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 24434Potassium NitrateHCID 134698161-isopropyl-1H-pyrazole

Product 1

HCID 134698241-Isopropyl-4-nitro-1H-pyrazoleYield 46%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 1-isopropyl-1H-pyrazole (5 g, 45.5 mmol) in conc. H2SO4 (50 mL) was added KNO3 (5.0 go, 50 mmol) portionwise at 0° C. After the addition, the resulting mixture was heated to 50° C. for 8 h. The reaction mixture was cooled to RT, poured into ice water, and the mixture was extracted with EtOAc. The combined organics were washed with saturated Na2CO3 solution, brine, dried (Na2SO4), concentrated in vacuo and purified via column chromatography to provide 1-isopropyl-4-nitro-1H-pyrazole (3.2 g, 46% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.99 (s, 1 H), 8.32 (s, 1H), 4.65 (m, 1 H), 1.51 (d, J=6.8 Hz, 6 H).

Workup

  1. additionAfter the addition
  2. temperatureThe reaction mixture was cooled to RT
  3. extractionthe mixture was extracted with EtOAc
  4. washThe combined organics were washed with saturated Na2CO3 solution, brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo
  7. custompurified via column chromatography

Sources & evidence

ORD record
ord-52e079e09f4e4609ae4afaa31dd22fa5
Source dataset
uspto-grants-2012_03
Patent number
US08143293B2

Reaction notes

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