4-Methylmorpholine → N,N-dihexyl-1,2-dihydro-2-oxoquinoline-3-carboxamide

HRID 2269618

Reaktionsgleichung

Reaktionsgleichung von HRID 2269618
[O:1]=[C:2]1[C:11]([C:12]([OH:14])=O)=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[NH:3]1.CN1CCOCC1.C(Cl)(=O)OCC(C)C.[CH2:30]([NH:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42])[CH2:31][CH2:32][CH2:33][CH2:34][CH3:35]>O1CCCC1.CN(C)C=O>[CH2:37]([N:36]([CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[C:12]([C:11]1[C:2](=[O:1])[NH:3][C:4]2[C:9]([CH:10]=1)=[CH:8][CH:7]=[CH:6][CH:5]=2)=[O:14])[CH2:38][CH2:39][CH2:40][CH2:41][CH3:42]

Komponenten

7

Edukt 4

HCID 79724-MethylmorpholineHCID 8920DihexylamineHCID 62365Isobutyl chloroformateHCID 3324882-Quinolone-3-carboxylic acid

Produkt 1

HCID 15461775N,N-dihexyl-1,2-dihydro-2-oxoquinoline-3-carboxamideAusbeute 75,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-15 °C

Versuchsvorschrift

In a mixture of 50 ml of tetrahydrofuran and 250 ml of N,N-dimethylformamide were dissolved 9.46 g of 1,2-dihydro-2-oxoquinoline-3-carboxylic acid and 5.06 g of N-methylmorpholine, and after cooling to −15° C., 6.83 g of isobutyl chlorocarbonate was added dropwise over 10 minutes. After stirring at −15° C. for 10 minutes, 9.73 g of dihexylamine was added dropwise over 5 minutes. After stirring at −15° C. for 4 hours and then at room temperature overnight, the reaction mixture was concentrated under reduced pressure, and the residue, after addition of ethyl acetate, was washed with water, 1N hydrochloric acid, a saturated aqueous sodium bicarbonate solution and a saturated aqueous sodium chloride solution, and dried over anhydrous sodium sulfate. After removal of the drying agent by filtration, the filtrate was concentrated under reduced pressure. The residue was recrystallized from hexane to give 13.51 g of N,N-dihexyl-1,2-dihydro-2-oxoquinoline-3-carboxamide.

Aufarbeitung

  1. stirringAfter stirring at −15° C. for 4 hours
  2. concentrationat room temperature overnight, the reaction mixture was concentrated under reduced pressure
  3. additionthe residue, after addition of ethyl acetate
  4. washwas washed with water, 1N hydrochloric acid
  5. dry with materiala saturated aqueous sodium bicarbonate solution and a saturated aqueous sodium chloride solution, and dried over anhydrous sodium sulfate
  6. customAfter removal of the drying agent
  7. filtrationby filtration
  8. concentrationthe filtrate was concentrated under reduced pressure
  9. customThe residue was recrystallized from hexane

Quellen und Nachweise

ORD-Eintrag
ord-29bf628c2e574a03b0bbbdf8a4b778be
Quelldatensatz
uspto-grants-2001_12
Patentnummer
US06329525B1

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