Methyl quinoline-5-carboxylate → Methyl 5,6,7,8-tetrahydroquinoline-5-carboxylate

HRID 2175905Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2175905
[N:1]1[C:10]2[CH:9]=[CH:8][CH:7]=[C:6]([C:11]([O:13][CH3:14])=[O:12])[C:5]=2[CH:4]=[CH:3][CH:2]=1>C(O)(C(F)(F)F)=O.[Pt]=O>[N:1]1[C:10]2[CH2:9][CH2:8][CH2:7][CH:6]([C:11]([O:13][CH3:14])=[O:12])[C:5]=2[CH:4]=[CH:3][CH:2]=1

Komponenten

4

Edukt 1

HCID 12503486Methyl quinoline-5-carboxylate

Produkt 1

HCID 77230270Methyl 5,6,7,8-tetrahydroquinoline-5-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 82844Platinum oxide (PtO)KatalysatorHCID 6422Trifluoroacetic acidLösungsmittel

Versuchsvorschrift

Methyl quinoline-5-carboxylate (3.67 g, 19.61 mmol) was dissolved in TFA (60 mL) and added platinum oxide (0.49 g, 2.16 mmol) then hydrogenated at room temperature overnight. The catalyst was filtered off and the filtrate was evaporated to dryness. The residue was chromatographed through a 120 g ISCO Redi-sep column and eluted with 5% of (10% NH4OH in MeOH) in DCM to yield methyl 5,6,7,8-tetrahydroquinoline-5-carboxylate: LC-MS: M+1=192.

Aufarbeitung

  1. filtrationThe catalyst was filtered off
  2. customthe filtrate was evaporated to dryness
  3. customThe residue was chromatographed through a 120 g ISCO Redi-sep column
  4. washeluted with 5% of (10% NH4OH in MeOH) in DCM

Quellen und Nachweise

ORD-Eintrag
ord-dbff58fd7fd348a78a6fd0c71d2b2075
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09062070B2

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