Thionyl Chloride → 7-Benzyloxy-4-chloro-6-methoxyquinoline hydrochloride

HRID 393597Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 393597
[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13](=O)[CH:14]=[CH:15][NH:16]2)=[CH:11][C:10]=1[O:20][CH3:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)([Cl:24])=O>CN(C=O)C>[ClH:24].[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([Cl:24])=[CH:14][CH:15]=[N:16]2)=[CH:11][C:10]=1[O:20][CH3:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 24386Thionyl ChlorideHCID 226465797-(Benzyloxy)-6-methoxyquinolin-4-ol

Produkt 1

HCID 226465617-Benzyloxy-4-chloro-6-methoxyquinoline hydrochlorideAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A suspension of 7-benzyloxy-6-methoxy-1,4-dihydroquinolin-4-one (3.37 g, 13 mmol) in thionyl chloride (50 ml) and DMF (0.25 ml) was heated at reflux for 1 hour. Excess thionyl chloride was removed by evaporation and the residue azeotroped with toluene and triturated with ether, the product collected by filtration and dried under vacuum to give 7-benzyloxy-4-chloro-6-methoxyquinoline hydrochloride (3.9 g, 89%).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux for 1 hour
  3. customExcess thionyl chloride was removed by evaporation
  4. customthe residue azeotroped with toluene
  5. customtriturated with ether
  6. filtrationthe product collected by filtration
  7. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-094caedd26f4441b8cddbeec629c37ed
Quelldatensatz
uspto-grants-2004_10
Patentnummer
US06809097B1

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