Carbon Dioxide → HCID 12278957, Verbindung

HRID 971486

Reaktionsgleichung

Reaktionsgleichung von HRID 971486
[N:1]1[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.C1([Li])C=CC=CC=1.BrC1C=CC=CC=1.[Li].[Li][CH:27]1C2N=CC=CC=2CCC1.[C:37](=[O:39])=[O:38]>CCOCC>[CH3:27][O:38][C:37]([CH:9]1[C:10]2[N:1]=[CH:2][CH:3]=[CH:4][C:5]=2[CH2:6][CH2:7][CH2:8]1)=[O:39]

Komponenten

8

Edukt 6

HCID 280Carbon DioxideHCID 7961BromobenzeneHCID 663355,6,7,8-TetrahydroquinolineHCID 3028194LithiumHCID 178506676HCID 178506676, VerbindungHCID 178506835HCID 178506835, Verbindung

Produkt 1

HCID 12278957HCID 12278957, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel2×

Versuchsvorschrift

A solution of 5,6,7,8-tetrahydroquinoline (14 g.) in dry ether (100 ml.) was added dropwise over 1/2 hour to an ethereal solution of phenyl lithium (prepared from bromobenzene (42 g.) and lithium (3.7 g.) in dry ether (300 ml.) and the reaction mixture stirred at room temperature for a further one hour. The cooled reaction mixture containing 8-lithio-5,6,7,8-tetrahydroquinoline was saturated with dry CO2 gas, evaporated in vacuo and the residue treated with methanol previously saturated with dry HCl (500 ml.) giving methyl-5,6,7,8-tetrahydroquinoline-8-carboxylate as described in our copending U.S. Ser. No. 460,265.

Aufarbeitung

  1. customThe cooled reaction mixture
  2. customevaporated in vacuo
  3. additionthe residue treated with methanol previously saturated with dry HCl (500 ml.)

Quellen und Nachweise

ORD-Eintrag
ord-683b73d089a24546a8c30887a6140537
Quelldatensatz
uspto-grants-1979_07
Patentnummer
US04160094

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