Hydrochloric Acid → HCID 20375617, Verbindung

HRID 1448832Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1448832
C([O:8][CH2:9][CH2:10][C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[C:18]([F:21])[CH:19]=2)[N:14]([CH2:22][C:23]2[CH:28]=[C:27]([Br:29])[C:26]([Br:30])=[C:25]([Br:31])[CH:24]=2)[C:13](=[O:32])[CH:12]=1)C1C=CC=CC=1.C(O)C.Cl>O1CCOCC1.[Pd]>[OH:8][CH2:9][CH2:10][C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[C:18]([F:21])[CH:19]=2)[N:14]([CH2:22][C:23]2[CH:28]=[C:27]([Br:29])[C:26]([Br:30])=[C:25]([Br:31])[CH:24]=2)[C:13](=[O:32])[CH:12]=1

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 20375643HCID 20375643, Verbindung

Produkt 1

HCID 20375617HCID 20375617, VerbindungAusbeute 71 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A solution of 4-(2-benzyloxyethyl)-6-fluoro-1-(3,4,5-tribromobenzyl)-1,2-dihydro-2-oxoquinoline (6.0 g.) in a mixture of dioxan (50 ml.), ethanol (50 ml.), and concentrated hydrochloric acid (2 ml.) was hydrogenated at atmospheric pressure over 5% palladium on carbon (1 g.). The theoretical quantity of hydrogen (390 ml. at N.T.P.) was absorbed in four minutes. The hydrogenation was stopped and the mixture filtered. Evaporation of the filtrate gave the crude product which was recrystallised twice from methanol to give 4-(2-hydroxyethyl)-6-fluoro-1-(3,4,5-tribromobenzyl)-1,2-dihydro-2-oxoquinoline, m.p. 199°-201° C., in 71% yield.

Aufarbeitung

  1. customThe theoretical quantity of hydrogen (390 ml. at N.T.P.) was absorbed in four minutes
  2. filtrationthe mixture filtered
  3. customEvaporation of the filtrate
  4. customgave the crude product which
  5. customwas recrystallised twice from methanol

Quellen und Nachweise

ORD-Eintrag
ord-e5f318db9e7a466db26eaf2ce364f3d7
Quelldatensatz
uspto-grants-1980_02
Patentnummer
US04187310

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