Diethyl (ethoxymethylene)malonate → Ethyl 7-chloro-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate

HRID 544217Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 544217
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[F:9])[NH2:5].CC[O:12][CH:13]=[C:14]([C:20](OCC)=O)[C:15]([O:17][CH2:18][CH3:19])=[O:16]>>[CH2:18]([O:17][C:15]([C:14]1[C:13](=[O:12])[C:6]2[C:4](=[CH:3][C:2]([Cl:1])=[C:8]([F:9])[CH:7]=2)[NH:5][CH:20]=1)=[O:16])[CH3:19]

Komponenten

3

Edukt 2

HCID 6871Diethyl (ethoxymethylene)malonateHCID 97083-Chloro-4-fluoroaniline

Produkt 1

HCID 3018009Ethyl 7-chloro-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylateAusbeute 118,8 %

Versuchsvorschrift

A mixture of 3-chloro-4-fluoroaniline (1.46 g) and diethyl ethoxymethylene malonate (2.16 g) was heated at 120°-130° C. After 2 hours, the resulting ethanol was evaporated off. The residue was added to diphenyl ether (50 ml) and refluxed for 1 hour. After the solution cooled, the resulting precipitate was filtered, washed with benzene, and dried. The solid was recrystallized from N,N-dimethylformamide (DMF) to give 7-chloro-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid ethyl ester (3.2 g).

Aufarbeitung

  1. temperaturewas heated at 120°-130° C
  2. customthe resulting ethanol was evaporated off
  3. additionThe residue was added to diphenyl ether (50 ml)
  4. temperaturerefluxed for 1 hour
  5. temperatureAfter the solution cooled
  6. filtrationthe resulting precipitate was filtered
  7. washwashed with benzene
  8. customdried
  9. customThe solid was recrystallized from N,N-dimethylformamide (DMF)

Quellen und Nachweise

ORD-Eintrag
ord-eb39096b5fc940ca8040cbf13a35ff4c
Quelldatensatz
uspto-grants-1984_05
Patentnummer
US04448962

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