Hydrochloric Acid → Ethyl 1-cyclopropyl-8-(difluoromethoxy)-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate

HRID 2226488

Reaktionsgleichung

Reaktionsgleichung von HRID 2226488
[CH:1]1([NH:4][CH:5]=[C:6]([C:12](=[O:26])[C:13]2[CH:18]=[C:17]([F:19])[C:16]([F:20])=[C:15]([O:21][CH:22]([F:24])[F:23])[C:14]=2F)[C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:3][CH2:2]1.[H-].[Na+].Cl>C(OCC)C>[CH:1]1([N:4]2[C:14]3[C:13](=[CH:18][C:17]([F:19])=[C:16]([F:20])[C:15]=3[O:21][CH:22]([F:24])[F:23])[C:12](=[O:26])[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:5]2)[CH2:3][CH2:2]1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 178471879HCID 178471879, Verbindung

Produkt 1

HCID 15023786Ethyl 1-cyclopropyl-8-(difluoromethoxy)-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

The whole of the ethyl 3-cyclopropylamino-2-(3-difluoromethoxy-2,4,5-trifluorobenzoyl)acrylate [(XIX), R1 =--OCHF2, R3' =H, R17 =C2H5, X=X'=F] [prepared as described in step (c) anove] was dissolved in 150 ml of anhydrous diethyl ether, and then 0.39 g (0.0098 moles) of a 60% w/w suspension of sodium hydride in mineral oil was added in portions, whilst stirring at room temperature, to the resulting solution. After completion of the addition, the stirring was continued at room temperature for an additional 1 hour, and then the mixture was acidified by the addition of 1N aqueous hydrochloric acid with vigorous stirring. The reaction mixture was filtered and washed with water and with diethyl ether, in that order, to give 1.44 g of ethyl 1-cyclopropyl-8-difluoromethoxy-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate as colorless needles, melting at 224°-226° C.

Aufarbeitung

  1. additionwas added in portions
  2. additionAfter completion of the addition
  3. filtrationThe reaction mixture was filtered
  4. washwashed with water and with diethyl ether, in that order

Quellen und Nachweise

ORD-Eintrag
ord-4dba459f21784a95a131590b4d211654
Quelldatensatz
uspto-grants-1994_09
Patentnummer
US05348961

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