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Potassium Carbonate → methyl 2-{4-[N-(6-chloro-2-quinolinyl)-N-methylamino]-phenoxy}propionate

HRID 326048
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 326048
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([N:12]([C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=1)[CH3:13])[CH:6]=[CH:5]2.Br[CH:22]([CH3:27])[C:23]([O:25][CH3:26])=[O:24].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([N:12]([C:14]1[CH:19]=[CH:18][C:17]([O:20][CH:22]([CH3:27])[C:23]([O:25][CH3:26])=[O:24])=[CH:16][CH:15]=1)[CH3:13])[CH:6]=[CH:5]2
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Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 95576Methyl 2-bromopropionateHCID 204619604-[N-(6-chloro-2-quinolinyl)-N-methylamino]phenol

Produkt 1

HCID 20461952methyl 2-{4-[N-(6-chloro-2-quinolinyl)-N-methylamino]-phenoxy}propionate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

A mixture of 4-[N-(6-chloro-2-quinolinyl)-N-methylamino]phenol (1.1 g), methyl 2-bromopropionate (1.3 ml), anhydrous potassium carbonate (0.7 g) and acetone (20 ml) was heated under reflux with stirring for a period of 16 hours. The acetone was removed by distillation under reduced pressure and the residue was partitioned between water and chloroform. The chloroform extracts were dried (anhydrous MgSO4) and the solvent was evaporated. The residue was chromatographed over silica gel (40 g) with chloroform elution to give methyl 2-{4-[N-(6-chloro-2-quinolinyl)-N-methylamino]-phenoxy}propionate (1.05 g) as a colourless oil. Proton magnetic resonance spectrum (CDCl3 ; δ ppm); 8.0-6.6 (9H, m, quinoline and phenoxy protons); 4.9 (1H, q, CH--CH3); 3.9 (3H, s, OCH3); 3.6 (3H, s, N--CH3); 1.6 (3H, d, CHCH3).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureunder reflux
  3. customThe acetone was removed by distillation under reduced pressure
  4. customthe residue was partitioned between water and chloroform
  5. dry with materialThe chloroform extracts were dried (anhydrous MgSO4)
  6. customthe solvent was evaporated
  7. customThe residue was chromatographed over silica gel (40 g) with chloroform elution

Quellen und Nachweise

ORD-Eintrag
ord-737c422981d1403280fc4fb038e5e499
Quelldatensatz
uspto-grants-1984_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04444584

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