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

HRID 49935

Reaction equation

HRID 49935 reaction equation
[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

Participants

5

Reactant 2

HCID 946706-Quinolinecarboxylic acid, ethyl esterHCID 4311764Sodium borohydride

Product 1

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

Reagents, catalysts & solvents 2

HCID 11791229Dichloronickel;hexahydrateCatalystHCID 887MethanolSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-4e6a8430b1e340cdad7e86ff4ab13562
Source dataset
uspto-grants-2004_03
Patent number
US06710056B2

Linked notes

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