6-Bromo-4-chloroquinoline → 6-Bromo-4-cyclohexylmethoxy-quinoline

HRID 852993Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 852993
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[C:5]2Cl.[CH:13]1([CH2:19][O-:20])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1.[Na+]>C1(CO)CCCCC1.O>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[C:5]2[O:20][CH2:19][CH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1

Komponenten

5

Edukt 2

HCID 51395376-Bromo-4-chloroquinolineHCID 69464742HCID 69464742, Verbindung

Produkt 1

HCID 586153676-Bromo-4-cyclohexylmethoxy-quinolineAusbeute 71,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 7507CyclohexanemethanolLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

To a solution of 6-bromo-4-chloro-quinoline (0.550 g, 2.27 mmol) in cyclohexylmethanol (5 mL) was added a solution of sodium cyclohexylmethoxide (11.34 mmol, prepared from cyclohexylmethanol and sodium) at room temperature. Then, the reaction mixture was heated to 120° C. for 15 h in a sealed reaction flask. After cooling to room temperature, the reaction mixture was diluted with water and the solvent was removed under the vacuum. Then, the remaining aqueous solution was neutralized with 3.0N hydrochloric acid and the organic compound was extracted into ethyl acetate (3×50 mL). The combined extracts were washed with brine solution and dried over anhydrous magnesium sulfate. After filtration of the drying agent, the filtrate was removed under the vacuum and the residue was purified by using a Biotage silica gel column chromatography to afford 0.518 g (71% yield) of 6-bromo-4-cyclohexylmethoxy-quinoline as a light yellow oil: EI-HRMS m/e calcd for C16H18BrNO (M+) 320.2304, found 320.2314.

Aufarbeitung

  1. temperatureAfter cooling to room temperature
  2. customthe solvent was removed under the vacuum
  3. extractionthe organic compound was extracted into ethyl acetate (3×50 mL)
  4. washThe combined extracts were washed with brine solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationAfter filtration of the drying agent
  7. customthe filtrate was removed under the vacuum
  8. customthe residue was purified

Quellen und Nachweise

ORD-Eintrag
ord-1ae2af20a9da44eeb39ccd744460879d
Quelldatensatz
uspto-grants-2007_08
Patentnummer
US07253285B2

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