Hydrochloric Acid → HCID 20375617, Verbindung

HRID 1833389Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1833389
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 (6.0g.) in a mixture of dioxan (50ml.), ethanol (50ml.), and concentrated hydrochloric acid (2ml.) was hydrogenated at atmospheric pressure over 5% palladium on carbon (1g.). The theoretical quantity of hydrogen (390ml. 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 (390ml. 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-c89d49fbf2494bed8ff32e2280045a18
Quelldatensatz
uspto-grants-1978_01
Patentnummer
US04066651

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