Dichloromethane → Ethyl 2-{4-[(7-chloroisoquinolin-3-yl)oxy]phenoxy}propionate

HRID 647447Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 647447
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([O:12][C:13]3[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=3)[N:8]=[CH:9]2)=[CH:4][CH:3]=1.Br[CH:21]([CH3:27])[C:22]([O:24][CH2:25][CH3:26])=[O:23].C(=O)([O-])[O-].[K+].[K+].ClCCl>C(C(C)=O)C>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([O:12][C:13]3[CH:14]=[CH:15][C:16]([O:19][CH:21]([CH3:27])[C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:17][CH:18]=3)[N:8]=[CH:9]2)=[CH:4][CH:3]=1

Komponenten

6

Edukt 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 79040Ethyl 2-bromopropionateHCID 13386245HCID 13386245, Verbindung

Produkt 1

HCID 20484883Ethyl 2-{4-[(7-chloroisoquinolin-3-yl)oxy]phenoxy}propionateAusbeute 86,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6569Methyl Ethyl KetoneLösungsmittel

Versuchsvorschrift

4-[(7-chloroisoquinolin-3-yl)oxy]phenol (2.82 g) and ethyl 2-bromopropionate (2.07 g) in the presence of anhydrous potassium carbonate (1.58 g) were refluxed in methyl ethyl ketone (50 ml) for 4 hrs. The mixture was cooled, poured into dichloromethane, washed with water, dried (MgSO4) and evaporated. Purification by column chromatography over silica gel (eluant dichloromethane) gave ethyl 2-{4-[(7-chloroisoquinolin-3-yl)oxy]phenoxy}propionate (3.33 g) as a brown oil.

Aufarbeitung

  1. temperatureThe mixture was cooled
  2. washwashed with water
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customPurification by column chromatography over silica gel (eluant dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-ba578d89083c44f7a4185db7a988dd9b
Quelldatensatz
uspto-grants-1983_10
Patentnummer
US04409017

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