2-Isopropylquinoline → HCID 12229421, compound

HRID 33776Notes

Reaction equation

HRID 33776 reaction equation
[CH:1]([C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=1)([CH3:3])[CH3:2]>FC(F)(F)C(O)=O.O=[Pt]=O>[CH:1]([C:4]1[CH:13]=[CH:12][C:11]2[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[N:5]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 5133892-Isopropylquinoline

Product 1

HCID 12229421HCID 12229421, compound

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 6422Trifluoroacetic acidSolvent

Procedure

To a 0.23 M solution of 2-isopropylquinoline in trifluoroacetic acid in a Parr flask was added 0.1 equiv of PtO2. The suspension was set up on the Parr apparatus at 44 psi H2 overnight. After removal of the H2, CH2Cl2 was added, and the suspension was filtered through Celite. The solvent was removed under vacuum, and the residue was partitioned between EtOAc and saturated NaHCO3 solution. The organic layer was washed with H2O and brine, and was then dried over anhydrous MgSO4, filtered and evaporated to give the title compound as a tan colored oil.

Workup

  1. customwas set up on the Parr apparatus at 44 psi H2 overnight
  2. customAfter removal of the H2, CH2Cl2
  3. additionwas added
  4. filtrationthe suspension was filtered through Celite
  5. customThe solvent was removed under vacuum
  6. customthe residue was partitioned between EtOAc and saturated NaHCO3 solution
  7. washThe organic layer was washed with H2O and brine
  8. dry with materialwas then dried over anhydrous MgSO4
  9. filtrationfiltered
  10. customevaporated

Sources & evidence

ORD record
ord-9011adc8ebb24f91bdbda6a9f1d612e7
Source dataset
uspto-grants-2008_09
Patent number
US07429666B2

Reaction notes

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