Pyridine → 3,5-Dimethyl-1-phenyl-1H-pyrazole-4-carboxylic acid ethyl ester

HRID 413759

Reaktionsgleichung

Reaktionsgleichung von HRID 413759
[C:1]1([NH:7][NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:9]([O:11][C:12](=[O:20])[CH:13]([C:17](=O)[CH3:18])[C:14](=O)[CH3:15])[CH3:10].N1C=CC=CC=1>C(O)C>[CH2:9]([O:11][C:12]([C:13]1[C:14]([CH3:15])=[N:8][N:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:17]=1[CH3:18])=[O:20])[CH3:10]

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 7516PhenylhydrazineHCID 79063Ethyl 2-acetylacetoacetate

Produkt 1

HCID 6569643,5-Dimethyl-1-phenyl-1H-pyrazole-4-carboxylic acid ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

Similar to Example 1, phenyl hydrazine (7.5 mmol, 0.8 g) and 2-acetyl-3-oxo-butyric acid ethyl ester (7.5 mmol, 1.3 g) were mixed in a solution of 50% pyridine in ethanol. The solvents were removed under vacuum and the oil resuspended in chloroform. The resulting suspension was washed with 5% sodium bicarbonate, 5% hydrochloric acid, and then brine. The organic layer was dried over NaSO4, the solids filtered, and the solvents removed under vacuum. The crude material was purified over silica gel to yield the named product as an oil. 1H-NMR (CDCl3, ppm): 1.37 t (3H); 2.51 s (6H); 4.32 q (2H); 7.42 bs (5H).

Aufarbeitung

  1. customThe solvents were removed under vacuum
  2. washThe resulting suspension was washed with 5% sodium bicarbonate, 5% hydrochloric acid
  3. dry with materialThe organic layer was dried over NaSO4
  4. filtrationthe solids filtered
  5. customthe solvents removed under vacuum
  6. customThe crude material was purified over silica gel

Quellen und Nachweise

ORD-Eintrag
ord-270e03eb5a80411e818cd173dba9325d
Quelldatensatz
uspto-grants-2003_05
Patentnummer
US06569885B1

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