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

HRID 1789999Notes

Reaction equation

HRID 1789999 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 34 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 NH4 OH 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-e14ca53373f947628d9a61d018702f84
Source dataset
uspto-grants-2006_07
Patent number
US07071192B1

Reaction notes

Loading…