Water → 1-(3,4-dimethylphenyl)-5-hydroxy-3-methyl-1H-pyrazole-4-carbaldehyde

HRID 1814204Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1814204
P(Cl)(Cl)(Cl)=O.[CH3:6][C:7]1[CH:8]=[C:9]([N:14]2[C:18](=[O:19])[CH:17]=[C:16]([CH3:20])[NH:15]2)[CH:10]=[CH:11][C:12]=1[CH3:13].O.CN(C)[CH:24]=[O:25]>>[CH3:6][C:7]1[CH:8]=[C:9]([N:14]2[C:18](=[O:19])[C:17]([CH:24]=[O:25])=[C:16]([CH3:20])[NH:15]2)[CH:10]=[CH:11][C:12]=1[CH3:13]

Komponenten

5

Edukt 4

HCID 962WaterHCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 117358291-(3,4-Dimethylphenyl)-3-methyl-3-pyrazolin-5-one

Produkt 1

HCID 7591261-(3,4-dimethylphenyl)-5-hydroxy-3-methyl-1H-pyrazole-4-carbaldehydeAusbeute 79 %

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

Phosphorus oxychloride (4.82 mL, 51.6 mmol) was added dropwise to an ice-cooled, stirred suspension of 1-(3,4-dimethylphenyl)-3-methyl-3-pyrazolin-5-one (8.70 g, 43.0 mmol) in dimethylformamide (18.0 mL) at such a rate as to maintain the temperature below 20° C. After the addition, the mixture was heated at 100° C. for 2 h, then cooled, poured into iced water (200 mL). The resulting mixture was stirred for 18 h, then filtered. The solid was washed with water and dried to give the title compound (7.83 g, 79%) as a cream-coloured powder. 1H NMR (300 MHz, d6-DMSO) δ 9.63 (s, 1H), 7.47 (s, 1H), 7.41 (d, J=8.1 Hz, 1H), 2.23 (d, J=8.2 Hz, 1H), 2.34 (s, 3H), 2.27 (s, 3H), 2.25 (s, 3H).

Aufarbeitung

  1. temperaturecooled
  2. temperatureto maintain the temperature below 20° C
  3. additionAfter the addition
  4. temperaturecooled
  5. stirringThe resulting mixture was stirred for 18 h
  6. filtrationfiltered
  7. washThe solid was washed with water
  8. customdried

Quellen und Nachweise

ORD-Eintrag
ord-a6f7121e645448bf97cb8ab951701c2d
Quelldatensatz
uspto-grants-2005_04
Patentnummer
US06875786B2

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