Pyridine → 3,5-dimethyl-1-(2-nitrophenyl)-1H-pyrazole-4-carboxylic acid ethyl ester

HRID 8061

Reaktionsgleichung

Reaktionsgleichung von HRID 8061
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][NH2:11])([O-:3])=[O:2].[CH2:12]([O:14][C:15](=[O:23])[CH:16]([C:20](=O)[CH3:21])[C:17](=O)[CH3:18])[CH3:13].N1C=CC=CC=1>C(O)C.CCCCCC.C(Cl)(Cl)Cl>[CH2:12]([O:14][C:15]([C:16]1[C:17]([CH3:18])=[N:11][N:10]([C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N+:1]([O-:3])=[O:2])[C:20]=1[CH3:21])=[O:23])[CH3:13]

Komponenten

7

Edukt 3

HCID 1049PyridineHCID 79063Ethyl 2-acetylacetoacetateHCID 3314739(2-Nitrophenyl)hydrazine

Produkt 1

HCID 99657643,5-dimethyl-1-(2-nitrophenyl)-1H-pyrazole-4-carboxylic acid ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 702EthanolLösungsmittelHCID 6212ChloroformLösungsmittelHCID 8058HexaneLösungsmittel

Versuchsvorschrift

Similar to Example 1, o-nitrophenylhydrazine (20 mmol, 3.4 g) and 2-acetyl-3-oxo-butyric acid ethyl ester (20 mmol, 3.4 g) were mixed in a solution of 50% pyridine in ethanol and heated under reflux. The solvents then were removed under vacuum, and the residue was resuspended in chloroform. The resulting mixture was washed with water and dried over NaSO4. The solids then were filtered, and the solvents removed under vacuum. A precipitate formed when the oily solid was dissolved in a solution of 20% hexane in chloroform. The solid was collected and discarded, and the filtrate was purified over silica gel. The named product was contaminated, then was further purified by recrystallization from ethanol to yield a solid having a melting point of 128° C.–130° C.

Aufarbeitung

  1. temperatureheated
  2. temperatureunder reflux
  3. customThe solvents then were removed under vacuum
  4. washThe resulting mixture was washed with water
  5. dry with materialdried over NaSO4
  6. filtrationThe solids then were filtered
  7. customthe solvents removed under vacuum
  8. customA precipitate formed when the oily solid
  9. customThe solid was collected
  10. customthe filtrate was purified over silica gel
  11. customwas further purified by recrystallization from ethanol
  12. customto yield a solid

Quellen und Nachweise

ORD-Eintrag
ord-ca83e3a45b8246e188eadb65c21b8275
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07087634B2

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