Reaktionsgleichung
[CH3:1][C:2]([C:4]1[C:9]([Cl:10])=[CH:8][C:7]([Cl:11])=[C:6]([F:12])[CH:5]=1)=[O:3].[C:13](=O)([O:17]CC)[O:14][CH2:15][CH3:16].[H-].[Na+]>>[Cl:10][C:9]1[CH:8]=[C:7]([Cl:11])[C:6]([F:12])=[CH:5][C:4]=1[C:2]([CH2:1][C:13]([O:14][CH2:15][CH3:16])=[O:17])=[O:3]Komponenten
Versuchsvorschrift
Condensation of 2,4-dichloro-5-fluoroacetophenone 2 with diethyl carbonate in the presence of NaH yielded ethyl 2,4-dichloro-5-fluorobenzoylacetate 3. Treatment of the latter with triethyl orthoformate in acetic anhydride gave the carbon homologue enol ether intermediate 4 which was allowed to react with a slight excess of cyclopropylamine in methylene chloride at room temperature to give the enaminoketoester 5. Cyclization of the latter with 1 molar equivalent of NaH in refluxing dioxane yielded ethyl 1,4-dihydro-4-oxo-quinoline-3-carboxylate 6 which was then hydrolysed with aqueous NaOH to give 1-cyclopropyl-6-chloro-7-fluoro-1,4-dihydro-4-oxo-quinoline-3-carboxylic acid (IM) 7. See also Scheme 1 below (Maurer, F. and Grohe, K., DE 3 435 392 through Chem. Abst., Vol. 105, No.5, 1984, pp. 97158e). Compound data:
Quellen und Nachweise
- ORD-Eintrag
- ord-9e2ac241e38544f9a08bc006801f7437
- Quelldatensatz
- uspto-grants-2005_11
- Patentnummer
- US06967205B1
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