4-Methylphenylhydrazine monohydrochloride → 1-(4-Methylphenyl)pyrazolidin-3-one

HRID 133177

Reaktionsgleichung

Reaktionsgleichung von HRID 133177
Cl.[C:2]1([CH3:10])[CH:7]=[CH:6][C:5]([NH:8][NH2:9])=[CH:4][CH:3]=1.C1CCN2C(=NCCC2)CC1.Br[CH2:23][CH2:24][C:25](Cl)=[O:26]>C(Cl)Cl>[CH3:10][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:23][CH2:24][C:25](=[O:26])[NH:9]2)=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 125044-Methylphenylhydrazine monohydrochlorideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 84944Propanoyl chloride, 3-bromo-

Produkt 1

HCID 19134851-(4-Methylphenyl)pyrazolidin-3-oneAusbeute 19.455,801 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

10 g of p-tolylhydrazine hydrochloride are dissolved in 100 ml of anhydrous CH2Cl2. The solution is cooled to 0° C. and 19 ml of DBU and then 6.5 mg of 3-bromopropionyl chloride are added. The mixture is stirred at ambient temperature for one hour. The reaction medium is poured onto water, extraction is carried out with CH2Cl2 and then purification is carried out by chromatography on a silica column eluted with an AcOEt/petroleum ether (v/v; 50/50) mixture. 1.3 g of crystals are obtained.

Aufarbeitung

  1. additionThe reaction medium is poured onto water, extraction
  2. custompurification
  3. washeluted with an AcOEt/petroleum ether (v/v; 50/50) mixture

Quellen und Nachweise

ORD-Eintrag
ord-e0d1fe6a07a74c78a3121edd965e5815
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07390818B2

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