Hydrochloric Acid → 6-Fluoro-2-(4-(morpholinomethyl)phenyl)quinoline-4-carboxylic acid

HRID 516960

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.[O:13]1[CH2:18][CH2:17][N:16]([CH2:19][C:20]2[CH:25]=[CH:24][C:23]([C:26](=O)[CH3:27])=[CH:22][CH:21]=2)[CH2:15][CH2:14]1.[OH-:29].[K+].Cl>C(O)C.O>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]=[C:26]([C:23]1[CH:22]=[CH:21][C:20]([CH2:19][N:16]3[CH2:17][CH2:18][O:13][CH2:14][CH2:15]3)=[CH:25][CH:24]=1)[CH:27]=[C:5]2[C:6]([OH:11])=[O:29]

Komponenten

Reaktionsbedingungen

Temperatur: 125 °C

Versuchsvorschrift

In a 20 ml microwave vial, 5-fluoroisatin (650 mg, 4 mmol) was suspended in ethanol (7 ml), then, 1-[4-(morpholinomethyl)phenyl]ethanone (preparation 6) (863 mg, 4 mmol) was added followed by water (7 ml). To this suspension potassium hydroxide (2.21 g, 39 mmol) was added at room temperature. The microwave vial was sealed and the reaction mixture was heated at 125° C. for 20 min under microwave irradiation. The resulting solution was diluted with water (50 ml) and adjusted to pH 7-8 with 10% HCl. The resulting precipitate was filtered and washed with water (50 ml) and ethyl acetate (100 ml) to obtain the desired product as an off-white solid (1.1 g, Yield: 76%).

Aufarbeitung

customThe microwave vial was sealed
filtrationThe resulting precipitate was filtered
washwashed with water (50 ml) and ethyl acetate (100 ml)

Quellen und Nachweise

ORD-Eintrag: ord-5e4397e8cd224994be0546dd8b05d8e5
Quelldatensatz: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09115088B2

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