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

HRID 2173369Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2173369
[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. Filtered off the catalyst and 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 1H-NMR (600 MHz, CDCl3): δ ppm 8.42 (d, J=3.7 Hz, 1H), 7.485 (d, J=7.7 Hz, 1H), 7.06-7.08 (m, 1H), 3.82 (t, J=5.6 Hz, 1H), 3.72 (d, J=3.2 Hz, 3H), 3.02-2.93 (m, 1H), 2.88-2.93 (m, 1H), 2.16-2.20 (m, 1H), 1.97-2.05 (m, 2H), 1.85-1.90 (m, 1H); LC-MS: M+1=192.

Aufarbeitung

  1. filtrationFiltered off the catalyst
  2. customevaporated 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-a4fe317fdaa545aaa5520b558deab614
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09056859B2

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