Hydrochloric Acid → 2-{3-[2-(3,4-Dichlorophenyl)azetidin-1-yl]prop-1-ylamino}-1H-quinolin-4-one

HRID 430075Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 430075
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]2[CH2:12][CH2:11][N:10]2[CH2:13][CH2:14][CH2:15][NH:16][C:17]2[CH:26]=[C:25]([O:27]C)[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[N:18]=2)[CH:5]=[CH:6][C:7]=1[Cl:8].Cl>>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]2[CH2:12][CH2:11][N:10]2[CH2:13][CH2:14][CH2:15][NH:16][C:17]2[NH:18][C:19]3[C:24]([C:25](=[O:27])[CH:26]=2)=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH:5]=[CH:6][C:7]=1[Cl:8]

Komponenten

3

Edukt 2

HCID 313Hydrochloric AcidHCID 18353676HCID 18353676, Verbindung

Produkt 1

HCID 183536702-{3-[2-(3,4-Dichlorophenyl)azetidin-1-yl]prop-1-ylamino}-1H-quinolin-4-oneAusbeute 23,3 %

Versuchsvorschrift

2-{3-[2-(3,4-Dichlorophenyl)azetidin-1-yl]prop-1-ylamino}-4-methoxyquinoline (0.04 g, 0.096 mmol) was treated at reflux with 10M HCl (4 ml) for 45 min. The reaction mixture was evaporated to dryness, and the residue purified by chromatography on silica gel eluting with 10% (9:1 MeOH/NH3) in dichloromethane to give the title compound as a colourless gum (9 mg, 23%); δH (CD3OD) 1.75 (2H, m), 2.2 (1H, m), 2.45 (1H, m), 2.7-2.9 (2H, m), 3.05 (1H, m), 3.35 (2H, m), 3.55 (1H, m), 5.7 (1H, s), 7.3-7.5 (4H, m), 7.6-7.7 (2H, m), 8.1 (1H, dd); MS (ES+) 402/404 (53/39%, MH+), 230 (60), 187 (100).

Aufarbeitung

  1. customThe reaction mixture was evaporated to dryness
  2. customthe residue purified by chromatography on silica gel eluting with 10% (9:1 MeOH/NH3) in dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-8aa651ee50bd4d3782946a17f219a591
Quelldatensatz
uspto-grants-2001_11
Patentnummer
US06320051B1

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