Methanol → 1-methyl-6-[3-(quinolin-6-ylamino)propoxy]-1H-quinolin-2-one

HRID 69031

Reaktionsgleichung

Reaktionsgleichung von HRID 69031
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[CH:5]2.CO.I[CH2:15][CH2:16][CH2:17][O:18][C:19]1[CH:20]=[C:21]2[C:26](=[CH:27][CH:28]=1)[N:25]([CH3:29])[C:24](=[O:30])[CH:23]=[CH:22]2>ClCCl>[CH3:29][N:25]1[C:26]2[C:21](=[CH:20][C:19]([O:18][CH2:17][CH2:16][CH2:15][NH:1][C:2]3[CH:3]=[C:4]4[C:9](=[CH:10][CH:11]=3)[N:8]=[CH:7][CH:6]=[CH:5]4)=[CH:28][CH:27]=2)[CH:22]=[CH:23][C:24]1=[O:30]

Komponenten

5

Edukt 3

HCID 887MethanolHCID 113736-AminoquinolineHCID 669606076-(3-iodopropoxy)-1-methyl-1H-quinolin-2-one

Produkt 1

HCID 669615471-methyl-6-[3-(quinolin-6-ylamino)propoxy]-1H-quinolin-2-oneAusbeute 48 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

6-Aminoquinoline (360 mg) was added to the methanol solution (10 ml) of 6-(3-iodopropoxy)-1-methyl-1H-quinolin-2-one (172 mg) and stirred at 60° C. for 17 hours. The reaction mixture was added to ice water, and extraction with dichloromethane was performed. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:methanol=10:0→4:1). The purified product was condensed under reduced pressure to give the title compound (86.4 mg) as a yellow amorphous solid.

Aufarbeitung

  1. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (ethyl acetate:methanol=10:0→4:1)
  4. customcondensed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-2f6374596bc5445d870c3e670a90bc45
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08822453B2

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