3-Methoxy-2-methylquinoline → 5,6,7,8-Tetrahydro-3-methoxy-2-methylquinoline

HRID 2217299Notes

Reaction equation

HRID 2217299 reaction equation
[CH3:1][O:2][C:3]1[C:4]([CH3:13])=[N:5][C:6]2[C:11]([CH:12]=1)=[CH:10][CH:9]=[CH:8][CH:7]=2.[H][H]>FC(F)(F)C(O)=O.[Pd]>[CH3:1][O:2][C:3]1[C:4]([CH3:13])=[N:5][C:6]2[CH2:7][CH2:8][CH2:9][CH2:10][C:11]=2[CH:12]=1

Participants

5

Reactant 2

HCID 128209713-Methoxy-2-methylquinolineHCID 178418361HCID 178418361, compound

Product 1

HCID 220369935,6,7,8-Tetrahydro-3-methoxy-2-methylquinolineYield 99.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6422Trifluoroacetic acidSolvent

Procedure

A mixture of 3-methoxy-2-methylquinoline (0.081 mol) in trifluoro-acetic acid (150 ml) was hydrogenated at room temperature under a 3-4 bar pressure for 48 hours with palladium on activated carbon (2 g) as a catalyst. After uptake of hydrogen (2 equiv.), the catalyst was filtered through celite and washed with H2O. The filtrate was basified with a concentrated NH4OH solution and extracted with CH2Cl2. The organic layer was separated, dried (MgSO4), filtered and the solvent was evaporated, yielding 14.3 g (quant.) of 5,6,7,8-tetrahydro-3-methoxy-2-methylquinoline (interm. 13).

Workup

  1. washwashed with H2O
  2. extractionextracted with CH2Cl2
  3. customThe organic layer was separated
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customthe solvent was evaporated

Sources & evidence

ORD record
ord-33679a8fcd274e1f89f59253e774813d
Source dataset
uspto-grants-2008_08
Patent number
US07407969B2

Reaction notes

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