4-Benzylidene-2-(2-chloro-phenyl)-4H-oxazol-5-one → 3-Isoquinolinecarboxylicacid, 1-(2-chlorophenyl)-

HRID 44440

Reaktionsgleichung

Reaktionsgleichung von HRID 44440
[CH:1](=[C:8]1[C:12](=[O:13])[O:11][C:10]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[Cl:20])=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Al+3].[Cl-].[Cl-].[Cl-]>ClCC(Cl)(Cl)Cl>[Cl:20][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[C:10]1[C:7]2[C:2](=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:1]=[C:8]([C:12]([OH:11])=[O:13])[N:9]=1

Komponenten

4

Edukt 2

HCID 31092794-Benzylidene-2-(2-chloro-phenyl)-4H-oxazol-5-oneHCID 6451240Aluminum(III) Chloride

Produkt 1

HCID 110005543-Isoquinolinecarboxylicacid, 1-(2-chlorophenyl)-Ausbeute 35 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 124181,1,1,2-TetrachloroethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A solution of 22 (12 mmol) in tetrachloroethane was added to the suspension of AlCl3 (36 mmol) in tetrachloroethane (50 ml). The resulting mixture was heated to 60° C. for 1.5 hrs. The reaction mixture was quenched by addition of 1 M HCl (50 ml). Then, the mixture was basified by addition of NaOH (1M aqueous solution), the resulted layers were separated, and the aqueous layer was acidified by HCl (aqueous solution). This aqueous phase was extracted with CH2Cl2, dried over MgSO4 and finally the solvents were removed under reduced pressure, to give 35% yield of the desired product.

Aufarbeitung

  1. customThe reaction mixture was quenched by addition of 1 M HCl (50 ml)
  2. additionThen, the mixture was basified by addition of NaOH (1M aqueous solution)
  3. customthe resulted layers were separated
  4. extractionThis aqueous phase was extracted with CH2Cl2
  5. dry with materialdried over MgSO4
  6. customfinally the solvents were removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-35b8cd1e5e834e47815816d05cce98c3
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08541428B2

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