Hexane → 2-Chloroquinoline-3-carbonitrile

HRID 2413150

Reaktionsgleichung

Reaktionsgleichung von HRID 2413150
[C:1]([C:3]1[C:4](=O)[NH:5][C:6]2[C:11]([CH:12]=1)=[CH:10][CH:9]=[CH:8][CH:7]=2)#[N:2].P(Cl)(Cl)([Cl:16])=O.CCCCCC>C(Cl)Cl>[Cl:16][C:4]1[C:3]([C:1]#[N:2])=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=1

Komponenten

5

Edukt 3

HCID 8058HexaneHCID 24813Phosphorus oxychlorideHCID 27645772-Oxo-1,2-dihydroquinoline-3-carbonitrile

Produkt 1

HCID 115646012-Chloroquinoline-3-carbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of 50 g of 3-cyano-2(1H)-quinolinone and 250 ml of phosphoryl chloride was heated at reflux for 18 hours. Volatile material was evaporated from the mixture under reduced pressure and the resulting residue was carefully added to water. The solid which formed was separated by filtration, washed with water and dried to give crude product. This was dissolved in methylene chloride and the resulting solution was treated with silica gel and filtered to give a pale yellow solution. Hexane was added to the solution which was then placed on a steam bath until crystallization occurred. The solid was then separated by filtration to give 2-chloro-3-cyanoquinoline. This compound melts at about 163°-164° C.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux for 18 hours
  3. customVolatile material was evaporated from the mixture under reduced pressure
  4. additionthe resulting residue was carefully added to water
  5. customThe solid which formed
  6. customwas separated by filtration
  7. washwashed with water
  8. customdried
  9. customto give crude product
  10. additionthe resulting solution was treated with silica gel
  11. filtrationfiltered
  12. customto give a pale yellow solution
  13. customwas then placed on a steam bath until crystallization
  14. customThe solid was then separated by filtration

Quellen und Nachweise

ORD-Eintrag
ord-4a46d74d2f6f441e8616d6eb81c9f154
Quelldatensatz
uspto-grants-1985_01
Patentnummer
US04496569

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