Chlorosuccinimide → 8-Chloro-2-methylquinolin-7-ol

HRID 338999

Reaktionsgleichung

Reaktionsgleichung von HRID 338999
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][C:6]([OH:12])=[CH:7][CH:8]=2)[N:3]=1.[Cl:13]N1C(=O)CCC1=O>C(Cl)Cl.C(Cl)(Cl)Cl.[Cl-].[Zr+4].[Cl-].[Cl-].[Cl-]>[Cl:13][C:5]1[C:6]([OH:12])=[CH:7][CH:8]=[C:9]2[C:4]=1[N:3]=[C:2]([CH3:1])[CH:11]=[CH:10]2

Komponenten

6

Edukt 2

HCID 31398ChlorosuccinimideHCID 1354519692-Methylquinolin-7-ol

Produkt 1

HCID 1358589748-Chloro-2-methylquinolin-7-olAusbeute 55,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 9856075Zirconium chloride (ZrCl4), (T-4)-KatalysatorHCID 6212ChloroformLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

2-Methylquinolin-7-ol (200 mg, 1.26 mmol) was added to a solution of 1-chloropyrrolidine-2,5-dione (168 mg, 1.26 mmol) and zirconium(IV) chloride (14.6 mg, 0.0628 mmol) in DCM (10 mL) and the reaction was stirred at ambient temperature for 24 hours. The reaction was diluted with chloroform (30 mL) and washed with an aqueous sodium carbonate solution followed by brine. After drying (MgSO4), the solution was filtered and concentrated under reduced pressure and the residue was purified by reverse phase chromatography (SP4, 25 M, eluting with a gradient of water/ACN 90:10 to 0:100, 30 column volumes) to yield 8-chloro-2-methylquinolin-7-ol (134 mg, 55.1% yield) as a thick oil.

Aufarbeitung

  1. washwashed with an aqueous sodium carbonate solution
  2. dry with materialAfter drying (MgSO4)
  3. filtrationthe solution was filtered
  4. concentrationconcentrated under reduced pressure
  5. customthe residue was purified by reverse phase chromatography (SP4, 25 M
  6. washeluting with a gradient of water/ACN 90:10 to 0:100, 30 column volumes)

Quellen und Nachweise

ORD-Eintrag
ord-b3b18598e8a749c38eb447892a2ab23c
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08889704B2

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