Triethylamine → Ethyl 3,6-dimethylquinoline-2-carboxylate

HRID 1604545Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1604545
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH3:12])[CH:10]=2)[N:5]=[C:4]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:3]=1[CH3:18].C(N(CC)CC)C>[Pd].C(OCC)(=O)C>[CH3:18][C:3]1[C:4]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[N:5][C:6]2[C:11]([CH:2]=1)=[CH:10][C:9]([CH3:12])=[CH:8][CH:7]=2

Komponenten

5

Edukt 2

HCID 8471TriethylamineHCID 19603353Ethyl 4-chloro-3,6-dimethylquinoline-2-carboxylate

Produkt 1

HCID 19603373Ethyl 3,6-dimethylquinoline-2-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of ethyl 4-chloro-3,6-DIMETHYLQUINOLINE-2-carboxylate (3.0 g), triethylamine (2.4 ml) and 10% palladium on carbon (300 mg) in ethyl acetate (30 ml) was stirred for 4 hours at ambient temperature under hydrogen atmosphere. After filtration the filtrate was concentrated in vacuo and diluted with dichloromethane. The mixture was washed with saturated sodium bicarbonate solution and water, dried over magnesium sulfate and concentrated in vacuo. The residue was purified by flash chromatography (dichloromethane-ethyl acetate) to give ethyl 3,6-dimethylquinoline-2-carboxylate.

Aufarbeitung

  1. filtrationAfter filtration the filtrate
  2. concentrationwas concentrated in vacuo
  3. additiondiluted with dichloromethane
  4. washThe mixture was washed with saturated sodium bicarbonate solution and water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash chromatography (dichloromethane-ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-f356ade900ef435d95bb791f5fa11c51
Quelldatensatz
uspto-grants-1999_11
Patentnummer
US05994368

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