Potassium Carbonate → 6-[3-(1-Cyclohexyl-1H-tetrazol-5-yl) propoxy]-2(1H)-quinolinone

HRID 1277420Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1277420
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[CH:6]=[CH:5]2.C(=O)([O-])[O-].[K+].[K+].[CH:19]1([N:25]2[C:29]([CH2:30][CH2:31][CH2:32]Cl)=[N:28][N:27]=[N:26]2)[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1>CN(C)C=O>[CH:19]1([N:25]2[C:29]([CH2:30][CH2:31][CH2:32][O:1][C:2]3[CH:3]=[C:4]4[C:9](=[CH:10][CH:11]=3)[NH:8][C:7](=[O:12])[CH:6]=[CH:5]4)=[N:28][N:27]=[N:26]2)[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 1770652,6-DihydroxyquinolineHCID 52099225-(3-Chloropropyl)-1-cyclohexyltetrazole

Produkt 1

HCID 130210946-[3-(1-Cyclohexyl-1H-tetrazol-5-yl) propoxy]-2(1H)-quinolinoneAusbeute 50,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Into 200 ml of dimethylformamide, 3.2 g of 6-hydroxycarbostyril, 3.3 g of potassium carbonate and 7.7 g of 1-cyclohexyl-5-γ-chloropropyltetrazole are added and stirred for 4 hours at 70° to 80° C. After the reaction is completed, dimethylformamide is removed by distillation under reduced pressure. The residue thus obtained is then extracted with 300 ml of chloroform and the chloroform layer is washed with a diluted NaOH aqueous solution and with water and next dried with Na2SO4. After removal of the drying agent by filtration, then the mother liquor is concentrated and the residue is recrystallized from chloroform to obtain 3.54 g of 6-[3-(1-cyclohexyltetrazol-5-yl)propoxy]carbostyril, in the form of colorless needle-like crystals. Melting point: 211° to 212° C.

Aufarbeitung

  1. customdimethylformamide is removed by distillation under reduced pressure
  2. customThe residue thus obtained
  3. extractionis then extracted with 300 ml of chloroform
  4. washthe chloroform layer is washed with a diluted NaOH aqueous solution and with water
  5. dry with materialnext dried with Na2SO4
  6. customAfter removal of the drying agent
  7. filtrationby filtration
  8. concentrationthe mother liquor is concentrated
  9. customthe residue is recrystallized from chloroform

Quellen und Nachweise

ORD-Eintrag
ord-56395523b1cb475792e61432a035cb2b
Quelldatensatz
uspto-grants-1981_07
Patentnummer
US04277479

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