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

HRID 853263

Reaktionsgleichung

Reaktionsgleichung von HRID 853263
[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 Silysia 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 Silysia 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-a6bb6bfd89374a31b7a82c1c5daf6216
Quelldatensatz
uspto-grants-2007_08
Patentnummer
US07253286B2

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