Dimethylformamide → 5-methyl-3-(4-methyl-3-nitro-phenyl)-1H-pyrazole

HRID 539638

Reaktionsgleichung

Reaktionsgleichung von HRID 539638
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH3:9])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].CO[C:16]([N:20](C)C)(OC)[CH3:17].C[N:24](C=O)C>>[CH3:17][C:16]1[NH:20][N:24]=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([CH3:1])=[C:3]([N+:11]([O-:13])=[O:12])[CH:4]=2)[CH:9]=1

Komponenten

4

Edukt 3

HCID 6228DimethylformamideHCID 792463'-Nitro-4'-methylacetophenoneHCID 878351,1-Dimethoxyethyl(dimethyl)amine

Produkt 1

HCID 593775315-methyl-3-(4-methyl-3-nitro-phenyl)-1H-pyrazole

Versuchsvorschrift

A solution of 1-(4-methyl-3-nitro-phenyl)-ethanone and (1,1-dimethoxy-ethyl)-dimethyl-amine in DMF was heated at 90° C. for 3 hours, then cooled to room temperature. Solvent was removed under reduced pressure, and the residue was dissolved in a mixture of EtOH (25 ml) and THF (5 ml). The mixture was cooled to 0° C., and hydrazine hydrate (5 ml) at 0° C. was added. The mixture was stirred for 16 hours at room temperature, then concentrated under reduced pressure. The residue was purified by “flash chromatography” (0 to 30% EtOAc in hexanes) to give 8.5 g of 5-methyl-3-(4-methyl-3-nitro-phenyl)-1H-pyrazole as a yellowish solid, which was recrystallyzed from EtOAc to give 8.2 g of yellow powder.

Aufarbeitung

  1. customSolvent was removed under reduced pressure
  2. dissolutionthe residue was dissolved in a mixture of EtOH (25 ml) and THF (5 ml)
  3. temperatureThe mixture was cooled to 0° C.
  4. additionhydrazine hydrate (5 ml) at 0° C. was added
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by “flash chromatography” (0 to 30% EtOAc in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-db45aec6d893439587875242df22e5c5
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08871760B2

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