7-Methylquinoline → 7-Methyl-1,2,3,4-tetrahydroquinoline

HRID 1515332Notes

Reaction equation

HRID 1515332 reaction equation
[CH3:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1>CO.[Pd]>[CH3:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH2:8][NH:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 119277-Methylquinoline

Product 1

HCID 4586807-Methyl-1,2,3,4-tetrahydroquinolineYield 99.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 7-methylquinoline (2.00 g) in methanol (40 ml), 10% palladium on activated carbon (200 mg) was added and stirred overnight under a hydrogen atmosphere (60 psi) at room temperature. After the reaction mixture was filtered through celite, the solvent was distilled off under reduced pressure and the resulting residue was purified by silica gel column chromatography (eluting solvent: n-hexane:ethyl acetate=20:1 to 10:1) to give the titled compound, i.e., 7-methyl-1,2,3,4-tetrahydroquinoline (2.05 g) as a yellow oil.

Workup

  1. filtrationAfter the reaction mixture was filtered through celite
  2. distillationthe solvent was distilled off under reduced pressure
  3. customthe resulting residue was purified by silica gel column chromatography (eluting solvent: n-hexane:ethyl acetate=20:1 to 10:1)

Sources & evidence

ORD record
ord-47db28d475234f448b93f82a61268022
Source dataset
uspto-grants-2012_07
Patent number
US08222417B2

Reaction notes

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