Hydrochloric Acid → 8-Methoxy-1,2,3,4-tetrahydroquinoline

HRID 1972102

Reaktionsgleichung

Reaktionsgleichung von HRID 1972102
C([BH3-])#N.[Na+].[CH3:5][O:6][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:16]=1[N:15]=[CH:14][CH:13]=[CH:12]2.Cl.[OH-].[NH4+]>CCO.O>[CH3:5][O:6][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:16]=1[NH:15][CH2:14][CH2:13][CH2:12]2

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 14923Ammonium HydroxideHCID 703108-MethoxyquinolineHCID 5003444Sodium cyanoborohydride

Produkt 1

HCID 52003458-Methoxy-1,2,3,4-tetrahydroquinolineAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittel2×HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Add sodium cyanoborohydride (505 g, 8.11 mol) in EtOH (1 L) to a solution of 8-methoxy quinoline (425 g, 2.673 mol) in EtOH (9 L), and stir. Cool the reaction mixture to an internal temperature of 0° C. and add HCl (35%, 1.12 L, 10.962 mol) dropwise over 60 min so that the internal temperature did not rise above 20° C. Allow the reaction mixture to warm to ambient temperature and then heat to reflux for 2.5 hours. Cool to ambient temperature and stir overnight. Add ammonium hydroxide (25%, 1 L); dilute with water (15 L); and extract the mixture with dichloromethane (3×10 L). Combine the organic layers and dry over sodium sulfate. Remove the solids by filtration. Collect the filtrate and concentrate under reduced pressure to give a residue. Purify the residue by silica gel flash chromatography, eluting with ethyl acetate: hexane (1:10) to give the title compound (357 g, 82%). ESI (m/z) 164(M+H).

Aufarbeitung

  1. customdid not rise above 20° C
  2. temperatureto warm to ambient temperature
  3. temperatureheat
  4. temperatureto reflux for 2.5 hours
  5. temperatureCool to ambient temperature
  6. stirringstir overnight
  7. extractionand extract the mixture with dichloromethane (3×10 L)
  8. dry with materialCombine the organic layers and dry over sodium sulfate
  9. customRemove the solids
  10. filtrationby filtration
  11. customCollect the filtrate
  12. concentrationconcentrate under reduced pressure
  13. customto give a residue
  14. customPurify the residue by silica gel flash chromatography
  15. washeluting with ethyl acetate: hexane (1:10)

Quellen und Nachweise

ORD-Eintrag
ord-0c60f68931f74060a2c62cad70cdb324
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08431706B2

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