6-Quinolinecarboxylic acid, ethyl ester → Ethyl 1,2,3,4-tetrahydroquinoline-6-carboxylate

HRID 49935

Reaktionsgleichung

Reaktionsgleichung von HRID 49935
[BH4-].[Na+].[N:3]1[C:12]2[C:7](=[CH:8][C:9]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=1>O.O.O.O.O.O.[Ni](Cl)Cl.CO>[NH:3]1[C:12]2[C:7](=[CH:8][C:9]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:10][CH:11]=2)[CH2:6][CH2:5][CH2:4]1

Komponenten

5

Edukt 2

HCID 946706-Quinolinecarboxylic acid, ethyl esterHCID 4311764Sodium borohydride

Produkt 1

HCID 13951736Ethyl 1,2,3,4-tetrahydroquinoline-6-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11791229Dichloronickel;hexahydrateKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

257 mg (1.1 mmol) of nickel chloride hexahydrate and then 770 mg (20.3 mmol) of sodium borohydride were added to a mixture of 1.00 g (5.0 mmol) of ethyl quinoline-6-carboxylate and 15 ml of methanol under cooling with ice, and they were stirred at room temperature for 20 minutes. Methanol was evaporated, and the residue was purified by the silica gel column chromatography (hexane/ethyl acetate) to obtain the title compound.

Aufarbeitung

  1. temperatureunder cooling with ice, and they
  2. customMethanol was evaporated
  3. customthe residue was purified by the silica gel column chromatography (hexane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-4e6a8430b1e340cdad7e86ff4ab13562
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06710056B2

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