4-Chloro-2-methylquinoline → (3-(2-Dimethylamino-ethoxy)-4-methyl-phenyl)-(2-methyl-quinolin-4-yl)-amine

HRID 914964

Reaktionsgleichung

Reaktionsgleichung von HRID 914964
[CH3:1][N:2]([CH3:14])[CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]([CH:10]=[CH:11][C:12]=1[CH3:13])[NH2:9].Cl[C:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[N:19]=[C:18]([CH3:26])[CH:17]=1>CCO.Cl>[CH3:1][N:2]([CH3:14])[CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]([NH:9][C:16]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[N:19]=[C:18]([CH3:26])[CH:17]=2)[CH:10]=[CH:11][C:12]=1[CH3:13]

Komponenten

5

Edukt 2

HCID 779734-Chloro-2-methylquinolineHCID 392392273-(2-Dimethylamino-ethoxy)-4-methylaniline

Produkt 1

HCID 58958140(3-(2-Dimethylamino-ethoxy)-4-methyl-phenyl)-(2-methyl-quinolin-4-yl)-amineAusbeute 57,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of 9 (0.25 g, 1.29 mmol) and 5 (0.29 ml, 1.44 mmol) in EtOH (8 mL) were added 2 drops of conc. HCl. The mixture was heated under reflux overnight. After cooling to room temperature, EtOH was removed under reduced pressure. The residue was partitioned between sat. NaHCO3 (aq.) and EtOAc (100 mL each) and the aquous layer was extracted with EtOAc (2×50 mL). The combined organic layers were dried over MgSO4, the solids were filtered, and the filtrate was concentrated under reduced pressure. The residue was purified on Florisil® (50% EtOAc/Hexanes to 15% MeOH/EtOAc) to yield the title compound as a light yellow solid (0.25 g).

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureunder reflux overnight
  3. customEtOH was removed under reduced pressure
  4. customThe residue was partitioned between sat. NaHCO3 (aq.) and EtOAc (100 mL each)
  5. extractionthe aquous layer was extracted with EtOAc (2×50 mL)
  6. dry with materialThe combined organic layers were dried over MgSO4
  7. filtrationthe solids were filtered
  8. concentrationthe filtrate was concentrated under reduced pressure
  9. customThe residue was purified on Florisil® (50% EtOAc/Hexanes to 15% MeOH/EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-6e6c6649663d451a9666e2bcb9ec1c8d
Quelldatensatz
uspto-grants-2007_09
Patentnummer
US07265122B2

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