Ethanol → 6,7-Dimethoxy-4-(3-aminopropoxy)quinoline

HRID 387741

Reaktionsgleichung

Reaktionsgleichung von HRID 387741
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][CH2:16][CH2:17][CH2:18][N:19]1C(=O)C2=CC=CC=C2C1=O.O.NN.C(O)C.CO>O1CCCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][CH2:16][CH2:17][CH2:18][NH2:19]

Komponenten

6

Edukt 4

HCID 702EthanolHCID 887MethanolHCID 24654Hydrazine hydrate (1:1)HCID 22936492N-(3-(6,7-dimethoxyquinolin-4-yloxy)propyl)phthalimide

Produkt 1

HCID 229362886,7-Dimethoxy-4-(3-aminopropoxy)quinoline

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

N-(3-(6,7-Dimethoxyquinolin-4-yloxy)propyl)phthalimide (600 mg, 1.53 mM), hydrazine monohydrate (300 mg, 6.12 mM), ethanol (5 ml), methanol (5 ml) and tetrahydrofuran (5 ml) were stirred for 2 hours under reflux. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel chromatography (Fuji Silicia NH Type Silica Gel, chloroform:methanol=20:1) to obtain the target substance (150 mg) as a brown oil.

Aufarbeitung

  1. temperatureunder reflux
  2. distillationThe solvent was distilled off under reduced pressure
  3. customthe residue was purified by silica gel chromatography (Fuji Silicia NH Type Silica Gel, chloroform:methanol=20:1)
  4. customto obtain the target substance (150 mg) as a brown oil

Quellen und Nachweise

ORD-Eintrag
ord-dfeaa0df382d454a858f69a7c6d066f9
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08372981B2

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