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

HRID 1098562Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1098562
[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]

Komponenten

4

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1118Sulfuric AcidLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-52e079e09f4e4609ae4afaa31dd22fa5
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08143293B2

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