Chloroform → HCID 14624973, Verbindung

HRID 703446Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 703446
O[CH2:2][CH2:3][CH:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7][C:6](=[O:14])[CH2:5]1.S(Cl)([Cl:17])=O.C(Cl)(Cl)Cl>N1C=CC=CC=1.O>[Cl:17][CH2:2][CH2:3][CH:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7][C:6](=[O:14])[CH2:5]1

Komponenten

6

Edukt 3

HCID 6212ChloroformHCID 24386Thionyl ChlorideHCID 14624972(+/-)-4-(2-hydroxyethyl)-3,4-dihydro-2(1H)-quinolinone

Produkt 1

HCID 14624973HCID 14624973, VerbindungAusbeute 88,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049PyridineKatalysatorHCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 5.2 g (0.027 mol) of (±)-4-(2-hydroxyethyl)-3,4-dihydro-2(1H)-quinolinone, 15 g (0.126 mol) of thionyl chloride, 200 ml of dry chloroform and 10 drops of pyridine is heated to reflux for 4 h. After the mixture is cooled, 50 ml of water are added dropwise and the mixture is stirred for 30 minutes. The organic phase is separated after settling has taken place, dried over magnesium sulphate and concentrated under vacuum. The residue is chromatographed on a silica column. Elution with a dichloromethane/acetone (90:10) mixture yields an oil which is crystallized in cyclohexane. 5 g (88%) of (±)-4-(2-chloroethyl)-3,4-dihydro-2(1H)-quinolinone, melting point 112°-113° C., are obtained.

Aufarbeitung

  1. temperatureis heated
  2. temperatureto reflux for 4 h
  3. temperatureAfter the mixture is cooled
  4. customThe organic phase is separated after settling
  5. dry with materialdried over magnesium sulphate
  6. concentrationconcentrated under vacuum
  7. customThe residue is chromatographed on a silica column
  8. washElution with a dichloromethane/acetone (90:10) mixture
  9. customyields an oil which
  10. customis crystallized in cyclohexane

Quellen und Nachweise

ORD-Eintrag
ord-f27660ff1f8e46a79d661309c3e4dcde
Quelldatensatz
uspto-grants-1991_01
Patentnummer
US04983607

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