Phosphorus oxychloride → 4-Chloroquinoline-8-carbonitrile

HRID 2060892Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2060892
O=[C:2]1[C:11]2[C:6](=[C:7]([C:12]#[N:13])[CH:8]=[CH:9][CH:10]=2)[NH:5][CH:4]=[CH:3]1.P(Cl)(Cl)([Cl:16])=O>>[Cl:16][C:2]1[C:11]2[C:6](=[C:7]([C:12]#[N:13])[CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1

Komponenten

3

Edukt 2

HCID 24813Phosphorus oxychlorideHCID 147925984-Hydroxy-8-cyanoquinoline

Produkt 1

HCID 147925994-Chloroquinoline-8-carbonitrile

Versuchsvorschrift

4-Oxo-1,4-dihydroquinoline-8-carbonitrile (0.40 g, 0.24 mmol, WO2004/113303) and phosphorous oxychloride (10 mL) were heated to 100° C. for 1.5 h. Solvent removed in vacuo. EtOAc (50 mL) was added and organic phase washed with sat. aqueous Na2CO3 solution, brine (20 mL) and dried (MgSO4). Solvent removed in vacuo to give the title compound: RT=3.09 min; m/z (ES+)=189.0 [M+H]+.

Aufarbeitung

  1. customSolvent removed in vacuo
  2. additionEtOAc (50 mL) was added
  3. washorganic phase washed with sat. aqueous Na2CO3 solution, brine (20 mL)
  4. dry with materialdried (MgSO4)
  5. customSolvent removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-43ccf59701574dd599a496da65d5fe42
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08278442B2

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