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Pyridine → tert-butyl 1-benzyl-8-(N-ethylacetamido)-2-oxo-1,2,3,4-tetrahydroquinolin-3-ylcarbamate

HRID 1887726
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1887726
[CH2:1]([N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][C:16]=2[NH:18][CH2:19][CH3:20])[CH2:11][CH:10]([NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[C:9]1=[O:29])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1[CH:35]=[CH:34]C=CC=1.C(Cl)(=[O:38])C>ClCCCl>[CH2:1]([N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][C:16]=2[N:18]([CH2:34][CH3:35])[C:19](=[O:38])[CH3:20])[CH2:11][CH:10]([NH:21][C:22](=[O:28])[O:23][C:24]([CH3:25])([CH3:27])[CH3:26])[C:9]1=[O:29])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 59620343Tert-butyl 1-benzyl-8-ethylamino-1,2,3,4-tetrahydro-2-oxoquinolin-3-ylcarbamate

Produkt 1

HCID 59620393tert-butyl 1-benzyl-8-(N-ethylacetamido)-2-oxo-1,2,3,4-tetrahydroquinolin-3-ylcarbamate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 111,2-Dichloroethane
Lösungsmittel
2×

Versuchsvorschrift

tert-Butyl 1-benzyl-8-ethylamino-1,2,3,4-tetrahydro-2-oxoquinolin-3-ylcarbamate (300 mg) was dissolved in 1,2-dichloroethane (2.5 mL), and pyridine (180 mg) was added to the solution. Under cooling on ice, a solution of acetyl chloride (179 mg) in 1,2-dichloroethane (2.5 mL) was added dropwise to the mixture. The resultant mixture was stirred at room temperature for two hours, and the reaction mixture was concentrated under reduced pressure. Water was added to the thus-recovered residue, and the mixture was subjected to extraction with ethyl acetate. The organic layer was sequentially washed with 0.1N HCl, saturated aqueous sodium bicarbonate solution, and saturated aqueous sodium chloride solution, and dried over sodium sulfate. Solvent was evaporated under reduced pressure, whereby the title compound (330 mg) was yielded.

Aufarbeitung

  1. temperatureUnder cooling on ice
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. additionWater was added to the thus-recovered residue
  4. extractionthe mixture was subjected to extraction with ethyl acetate
  5. washThe organic layer was sequentially washed with 0.1N HCl, saturated aqueous sodium bicarbonate solution, and saturated aqueous sodium chloride solution
  6. dry with materialdried over sodium sulfate
  7. customSolvent was evaporated under reduced pressure, whereby the title compound (330 mg)
  8. customwas yielded

Quellen und Nachweise

ORD-Eintrag
ord-c18bd312ccf841dbb908636aa0ca414d
Quelldatensatz
uspto-grants-2013_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08501772B2

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