6-Quinolinecarboxylic acid → 1,2,3,4-Tetrahydroquinoline-6-carboxylic acid

HRID 1770096Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1770096
[N:1]1[C:10]2[C:5](=[CH:6][C:7]([C:11]([OH:13])=[O:12])=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.C([O-])=O.[NH4+]>CO.[Pd]>[NH:1]1[C:10]2[C:5](=[CH:6][C:7]([C:11]([OH:13])=[O:12])=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1

Komponenten

5

Edukt 2

HCID 825716-Quinolinecarboxylic acidHCID 2723923Ammonium formate

Produkt 1

HCID 27796411,2,3,4-Tetrahydroquinoline-6-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

Quinoline-6-carboxylic acid (1.0 eq, 14.01 mmol) and ammonium formate (22 g, 350.1 mmol) were dissolved in MeOH (100 mL) and 10% Pd/C (4.04 g) was added. The solution was heated at reflux for 2.5 h then cooled to room temperature and filtered through celite. The solvent was removed to provide 1,2,3,4-tetrahydroquinoline-6-carboxylic acid in quantitative yield. 1H NMR (200 MHz, DMSO) δ1.78 (m, 2H), 2.65 ((m, 2H), 3.2 (m, 2H), 6.4 (m, 2H), 7.45 (m, 2H).

Aufarbeitung

  1. temperatureThe solution was heated
  2. temperatureat reflux for 2.5 h
  3. filtrationfiltered through celite
  4. customThe solvent was removed

Quellen und Nachweise

ORD-Eintrag
ord-217871c24d964720afadc059cd957f58
Quelldatensatz
uspto-grants-1995_01
Patentnummer
US05385909

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