Sodium Hydroxide → 7-Chloro-3-methyl-4-oxo-1-phenyl-1,4-dihydro-quinoline-2-carboxylic acid

HRID 1887791

Reaktionsgleichung

C[O:2][C:3]([C:5]1[N:6]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:7]2[C:12]([C:13](=[O:16])[C:14]=1[CH3:15])=[CH:11][CH:10]=[C:9]([Cl:17])[CH:8]=2)=[O:4].[OH-].[Na+].O1CCOCC1>C(OCC)(=O)C>[Cl:17][C:9]1[CH:8]=[C:7]2[C:12]([C:13](=[O:16])[C:14]([CH3:15])=[C:5]([C:3]([OH:4])=[O:2])[N:6]2[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:11][CH:10]=1

Komponenten

Reaktionsbedingungen

Temperatur: 150 °C

Versuchsvorschrift

In a sealed tube, 7-chloro-3-methyl-4-oxo-1-phenyl-1,4-dihydro-quinoline-2-carboxylic acid methyl ester (3.84 g, 11.7 mmol) and 1N sodium hydroxide (70 mL, 70 mmol) were added to dioxane (150 mL). The reaction mixture was heated to 150° C. overnight. The reaction mixture was poured into 500 mL ethyl acetate and extracted with 1N HCl (1×400 mL) and brine (1×100 mL). The organic layers were dried over Na2SO4 and concentrated in vacuo. The crude material was triturated with diethyl ether (1×100 mL) to give 7-chloro-3-methyl-4-oxo-1-phenyl-1,4-dihydro-quinoline-2-carboxylic acid (3.40 g, 92.5% yield) as a white solid. MS calcd for C17H12ClNO3 [(M+H)+] 314, obsd. 314.

Aufarbeitung

extractionextracted with 1N HCl (1×400 mL) and brine (1×100 mL)
dry with materialThe organic layers were dried over Na2SO4
concentrationconcentrated in vacuo
customThe crude material was triturated with diethyl ether (1×100 mL)

Quellen und Nachweise

ORD-Eintrag: ord-d78e57207dda470086ee05141ea1f808
Quelldatensatz: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08501732B2

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