Hydrochloric Acid → 2-(2-Chloro-4-(morpholinomethyl)phenyl)-6-fluoroquinoline-4-carboxylic acid

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Reaktionsgleichung

[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2=O.[Cl:13][C:14]1[CH:19]=[C:18]([CH2:20][N:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)[CH:17]=[CH:16][C:15]=1[C:27](=O)[CH3:28].[OH-:30].[K+].Cl>CCO.O.O>[Cl:13][C:14]1[CH:19]=[C:18]([CH2:20][N:21]2[CH2:22][CH2:23][O:24][CH2:25][CH2:26]2)[CH:17]=[CH:16][C:15]=1[C:27]1[CH:28]=[C:5]([C:6]([OH:11])=[O:30])[C:4]2[C:8](=[CH:9][CH:10]=[C:2]([F:1])[CH:3]=2)[N:7]=1

Komponenten

Reaktionsbedingungen

Temperatur: 125 °C

Versuchsvorschrift

A mixture of 5-fluoroisatin (702 mg, 4.25 mmol) and 1-(2-chloro-4-(morpholinomethyl)phenyl)ethanone (1.08 g, 4.25 mmol) (preparation 17) was prepared in EtOH/water (1:1) (10 ml) and then KOH (2.38 g, 42.49 mmol) was added and the resulting mixture heated under microwave irradiation at mw, 125° C. for 20 mins. The mixture was then diluted with water (10 ml) acidified to pH3 with 2M aqueous HCl, stirred for 16 h at room temperature and the resulting precipitate filtered, washed with water (2×10 ml) and concentrated under reduced pressure to afford 2-(2-chloro-4-(morpholinomethyl)phenyl)-6-fluoroquinoline-4-carboxylic acid as an orange solid (503 mg, 1.25 mmol, 30%).

Aufarbeitung

filtrationthe resulting precipitate filtered
washwashed with water (2×10 ml)
concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag: ord-ff0deb987adf456e96f53fdd808d7056
Quelldatensatz: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09115088B2

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