Hydroxyamine hydrochloride → 2-Chloroquinoline-3-carbonitrile

HRID 2413152

Reaktionsgleichung

Reaktionsgleichung von HRID 2413152
[Cl:1][C:2]1[C:11]([CH:12]=O)=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.Cl.[NH2:15]O>P(Cl)(Cl)(Cl)=O>[Cl:1][C:2]1[C:11]([C:12]#[N:15])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1

Komponenten

4

Edukt 2

HCID 443297Hydroxyamine hydrochlorideHCID 6909582-Chloro-3-quinolinecarboxaldehyde

Produkt 1

HCID 115646012-Chloroquinoline-3-carbonitrileAusbeute 71,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 24813Phosphorus oxychlorideLösungsmittel

Versuchsvorschrift

A mixture was prepared from 10 g of 2-chloro-3-quinolinecarboxaldehyde, 5.2 g of hydroxylamine hydrochloride and 100 ml of phosphoryl chloride and heated with a heat lamp. The mixture was heterogeneous until the temperature reached 90° C. and there was no noticeable exotherm or gas evolution. After heating at reflux for 30 minutes, the mixture was cooled for 16 hours. It was then quenched in 700 ml of water. The tan solid which formed was separated by filtration and dried to give 7 g of crude 2-chloro-3-cyanoquinoline.

Aufarbeitung

  1. temperatureheated with a heat lamp
  2. customreached 90° C.
  3. temperatureAfter heating
  4. temperatureat reflux for 30 minutes
  5. temperaturethe mixture was cooled for 16 hours
  6. customIt was then quenched in 700 ml of water
  7. customThe tan solid which formed
  8. customwas separated by filtration
  9. customdried

Quellen und Nachweise

ORD-Eintrag
ord-8445ec0f90394645a7e7b4ce05565a26
Quelldatensatz
uspto-grants-1985_01
Patentnummer
US04496569

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