Quinoline-3-carboxylic acid → 5,6,7,8-Tetrahydroquinoline-3-carboxylic acid

HRID 324518

Reaktionsgleichung

Reaktionsgleichung von HRID 324518
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([C:11]([OH:13])=[O:12])[CH:2]=1>FC(F)(F)C(O)=O.[Pt](=O)=O>[N:1]1[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[C:3]([C:11]([OH:13])=[O:12])[CH:2]=1

Komponenten

4

Edukt 1

HCID 80971Quinoline-3-carboxylic acid

Produkt 1

HCID 217959145,6,7,8-Tetrahydroquinoline-3-carboxylic acidAusbeute 43,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 345198Adams' catalystKatalysatorHCID 6422Trifluoroacetic acidLösungsmittel

Versuchsvorschrift

A mixture of 3-quinolinecarboxylic acid (1.73 g, 10.0 mmol) in trifluoroacetic acid (20 ml) with platinum dioxide (200 mg) was shaken in a Parr vessel at 10-15 psi. After 90 minutes the reaction mixture was filtered and the solvent removed in vacuo to yield an oil. The oil was added dropwise onto diethyl ether yielding a white solid which was collected by filtration and then recrystallised from ethyl acetate/hexane to yield the title compound as a white solid (770 mg).

Aufarbeitung

  1. filtrationAfter 90 minutes the reaction mixture was filtered
  2. customthe solvent removed in vacuo
  3. customto yield an oil
  4. additionThe oil was added dropwise onto diethyl ether yielding a white solid which
  5. filtrationwas collected by filtration
  6. customrecrystallised from ethyl acetate/hexane

Quellen und Nachweise

ORD-Eintrag
ord-292f9472f52d442095ef52e79c8a4349
Quelldatensatz
uspto-grants-2001_04
Patentnummer
US06218393B1

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