Potassium tert-butoxide → Ethyl 8-chloro-1-cyclopropyl-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate

HRID 476776

Reaktionsgleichung

[Cl:1][C:2]1[C:3](F)=[C:4]([CH:18]=[C:19]([F:22])[C:20]=1[F:21])[C:5]([C:7](=[CH:13][NH:14][CH:15]1[CH2:17][CH2:16]1)[C:8]([O:10][CH2:11][CH3:12])=[O:9])=[O:6].CC(C)([O-])C.[K+]>C(O)(C)(C)C>[Cl:1][C:2]1[C:20]([F:21])=[C:19]([F:22])[CH:18]=[C:4]2[C:3]=1[N:14]([CH:15]1[CH2:17][CH2:16]1)[CH:13]=[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:5]2=[O:6]

Komponenten

Reaktionsbedingungen

Temperatur: 6 °C

Versuchsvorschrift

To a solution of ethyl 2-(3-chloro-2,4,5-trifluorobenzoyl)-3-cyclopropylaminoacrylate in 40 ml of dry t-butanol is added a slurry of 1.20 g (10.7 mmol) of potassium t-butoxide in 20 ml of dry t-butanol. The reaction mixture is stirred at 6° C. for eight hours, then cooled to room temperature and concentrated. The residue is dissolved in chloroform, washed with water, dried over magnesium sulfate, filtered, and concentrated to give a pale brown solid. The crude product is purified by silica gel chromatography, and eluted with 80:20 chloroform:ethyl acetate to give 1.2 g of the title compound.

Aufarbeitung

temperaturecooled to room temperature
concentrationconcentrated
dissolutionThe residue is dissolved in chloroform
washwashed with water
dry with materialdried over magnesium sulfate
filtrationfiltered
concentrationconcentrated
customto give a pale brown solid
customThe crude product is purified by silica gel chromatography
washeluted with 80:20 chloroform

Quellen und Nachweise

ORD-Eintrag: ord-9b6bc155da43466689375b0b4950888a
Quelldatensatz: uspto-grants-1989_12
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US04885386

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