Isoamyl Nitrite → Ethyl 5-bromo-1-phenyl-1H-pyrazole-4-carboxylate

HRID 1731254

Reaktionsgleichung

Reaktionsgleichung von HRID 1731254
N[C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:5]=[CH:4][C:3]=1[C:13]([O:15][CH2:16][CH3:17])=[O:14].[Br:18]Br.N(OCCC(C)C)=O>C(Cl)(Cl)Cl>[Br:18][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:5]=[CH:4][C:3]=1[C:13]([O:15][CH2:16][CH3:17])=[O:14]

Komponenten

5

Edukt 3

HCID 8053Isoamyl NitriteHCID 24408BromineHCID 85270Ethyl 5-amino-1-phenyl-1H-pyrazole-4-carboxylate

Produkt 1

HCID 13802165Ethyl 5-bromo-1-phenyl-1H-pyrazole-4-carboxylateAusbeute 38 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

To a solution of 20.0 g of 5-amino-1-phenyl-1H-pyrazole-4-carboxylic acid, ethyl ester and 10 ml of bromine in 200 ml of chloroform was added 15.8 g of isoamyl nitrite dropwise. The reaction mixture was allowed to stir at room temperature for about 24 hours and the volatiles were removed under reduced pressure. The residue was recrystallized from ethanol/water to provide 10.0 g of 5-bromo-1-phenyl-1H-pyrazole-4-carboxylic acid, ethyl ester. Yield 38%. mp=86°-89° C.

Aufarbeitung

  1. customthe volatiles were removed under reduced pressure
  2. customThe residue was recrystallized from ethanol/water

Quellen und Nachweise

ORD-Eintrag
ord-118c0bca525843a6b756d8040708fa0c
Quelldatensatz
uspto-grants-1986_11
Patentnummer
US04620865

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