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Water → HCID 58307003, Verbindung

HRID 1909849
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1909849
[NH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH2:4][CH2:3][CH2:2]1.[H-].[Na+].BrC[CH2:20][C:21]1[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=1.O>CN(C=O)C.C(OCC)(=O)C>[Cl:27][C:24]1[CH:25]=[CH:26][C:21]([CH2:20][N:1]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][C:9]=3[C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH2:4][CH2:3][CH2:2]2)=[CH:22][CH:23]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 962WaterHCID 230291-(2-Bromoethyl)-4-chlorobenzeneHCID 24758Sodium hydride2×HCID 13951737Ethyl 1,2,3,4-tetrahydro-8-quinolinecarboxylate

Produkt 1

HCID 58307003HCID 58307003, VerbindungAusbeute 28,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228
Dimethylformamide
Lösungsmittel
2×
HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a mixture of ethyl 1,2,3,4-tetrahydroquinoline-8-carboxylate (1.1 g) and DMF (9.0 mL) was added sodium hydride (55% dispersion in paraffin liquid, 280 mg) at 0° C., followed by stirring at room temperature for 30 minutes. To the reaction mixture was added a solution of 1-(bromoethyl)-4-chlorobenzene (1.2 g) in DMF (2.0 mL) under ice-cooling, followed by stirring at room temperature for 3 days. To the reaction mixture was added sodium hydride (55% dispersion in paraffin liquid, 280 mg), followed by stirring for 1 day. To the reaction mixture were added water and ethyl acetate, and a liquid-separation operation was carried out. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-ethyl acetate) to obtain ethyl 1-(4-chlorobenzyl)-1,2,3,4-tetrahydroquinoline-8-carboxylate (510 mg).

Aufarbeitung

  1. temperaturecooling
  2. stirringby stirring at room temperature for 3 days
  3. stirringby stirring for 1 day
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationAfter filtration
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-3a909b71a8df457a80c4c3348f680c25
Quelldatensatz
uspto-grants-2013_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08598355B2

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