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Ethyl formate → 1-Cyclopropyl-6-fluoro-7-(4-formyl-3-methyl-1-piperazinyl)-5-methyl-4-oxo-3-formyl1,2,3,4-tetrahydroquinoline

HRID 1073760
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1073760
[CH:1]1([N:4]2[C:13]3[C:8](=[C:9]([CH3:22])[C:10]([F:21])=[C:11]([N:14]4[CH2:19][CH2:18][NH:17][CH:16]([CH3:20])[CH2:15]4)[CH:12]=3)[C:7](=[O:23])[CH2:6][CH2:5]2)[CH2:3][CH2:2]1.[CH3:24][O-:25].[Na+].[CH:27](OCC)=[O:28]>ClCCl>[CH:1]1([N:4]2[C:13]3[C:8](=[C:9]([CH3:22])[C:10]([F:21])=[C:11]([N:14]4[CH2:19][CH2:18][N:17]([CH:27]=[O:28])[CH:16]([CH3:20])[CH2:15]4)[CH:12]=3)[C:7](=[O:23])[CH:6]([CH:24]=[O:25])[CH2:5]2)[CH2:2][CH2:3]1
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Komponenten

5

Edukt 3

HCID 8025Ethyl formateHCID 10942334Sodium MethoxideHCID 157127231-Cyclopropyl-6-fluoro-7-(3-methyl-1-piperazinyl)5-methyl-4-oxo-1,2,3,4-tetrahydroquinoline

Produkt 1

HCID 157127251-Cyclopropyl-6-fluoro-7-(4-formyl-3-methyl-1-piperazinyl)-5-methyl-4-oxo-3-formyl1,2,3,4-tetrahydroquinolineAusbeute 65,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344
Dichloromethane
Lösungsmittel
2×

Versuchsvorschrift

1-Cyclopropyl-6-fluoro-7-(3-methyl-1-piperazinyl)5-methyl-4-oxo-1,2,3,4-tetrahydroquinoline (5.7 g) is dissolved in dichloromethane (200 ml) and thereto is added gradually sodium methylate (6.8 g) and further added dropwise a solution of ethyl formate (9.3 g) in dichloromethane (100 ml). The mixture is stirred at room temperature for one hour and then refluxed for one hour. After cooling, the reaction mixture is washed with water (200 ml) and dilute aqueous sodium hydroxide solution (200 ml) and extracted. The aqueous layer is taken and is made weakly acidic with diluted hydrochloric acid and extracted with dichloromethane. The extract is washed with water, dried and then dichloromethane is distilled off. The resulting residue is purified by silica gel column chromatography (eluent, chloroform) and recrystallized from diethyl ether - isopropanol to give 1-cyclopropyl-6-fluoro-7-(4-formyl-3-methyl-1-piperazinyl)-5-methyl-4-oxo-3-formyl1,2,3,4-tetrahydroquinoline (4.4 g) as yellow powdery crystals, m.p. 148°-150° C.

Aufarbeitung

  1. temperaturerefluxed for one hour
  2. temperatureAfter cooling
  3. washthe reaction mixture is washed with water (200 ml) and dilute aqueous sodium hydroxide solution (200 ml)
  4. extractionextracted
  5. extractionextracted with dichloromethane
  6. washThe extract is washed with water
  7. customdried
  8. distillationdichloromethane is distilled off
  9. customThe resulting residue is purified by silica gel column chromatography (eluent, chloroform)
  10. customrecrystallized from diethyl ether - isopropanol

Quellen und Nachweise

ORD-Eintrag
ord-db1329f4e4fa437faccb6f58cc25cfeb
Quelldatensatz
uspto-grants-1990_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04971970

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