Water → Ethyl 2-(4-phenyl-1H-pyrazol-1-yl)pyridine-3-carboxylate

HRID 1715164Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1715164
Cl[C:2]1[N:12]=[CH:11][CH:10]=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5].[C:13]1([C:19]2[CH:20]=[N:21][NH:22][CH:23]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C([O-])([O-])=O.[K+].[K+].O>CN(C)C=O.C1OCCOCCOCCOCCOCCOC1>[C:13]1([C:19]2[CH:20]=[N:21][N:22]([C:2]3[C:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])=[CH:9][CH:10]=[CH:11][N:12]=3)[CH:23]=2)[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Komponenten

7

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 1391064-PhenylpyrazoleHCID 2796614Ethyl chloronicotinate

Produkt 1

HCID 66719926Ethyl 2-(4-phenyl-1H-pyrazol-1-yl)pyridine-3-carboxylateAusbeute 79,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 2855718-Crown-6KatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

A mixture of 3.6 g of ethyl 2-chloronicotinate (19.4 mmol), 1.3 g of 4-phenylpyrazole (8.12 mmol), 4.4 g of K2CO3, 40 mg of 18-crown-6 and 30 mg of KI in 30 ml of N,N-dimethylformamide was stirred at 130° C. for 6 hours. For workup, H2O was added and, after extraction with ethyl acetate, the organic phase was washed with H2O and sat. NaCl solution. The crude product obtained after drying and concentration of the solution was purified by chromatography on silica gel (eluent: CH2Cl2/methanol 1-10%). In total, 1.9 g of an oil were obtained, which crystallized completely on standing in a refrigerator.

Aufarbeitung

  1. extractionafter extraction with ethyl acetate
  2. washthe organic phase was washed with H2O and sat. NaCl solution
  3. customThe crude product obtained
  4. customafter drying
  5. customconcentration of the solution was purified by chromatography on silica gel (eluent: CH2Cl2/methanol 1-10%)

Quellen und Nachweise

ORD-Eintrag
ord-cba6c79a94254532bd647b444a6b798a
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07799809B2

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