2-Methylquinoline → 5,6,7,8-Tetrahydro-2-methylquinoline

HRID 1178393Notes

Reaction equation

HRID 1178393 reaction equation
[N:1]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:2]=1[CH3:3].[H][H]>FC(F)(F)C(O)=O.O=[Pt]=O>[CH3:3][C:2]1[CH:4]=[CH:5][C:6]2[CH2:7][CH2:8][CH2:9][CH2:10][C:11]=2[N:1]=1

Participants

5

Reactant 2

HCID 70602-MethylquinolineHCID 178418361HCID 178418361, compound

Product 1

HCID 122294205,6,7,8-Tetrahydro-2-methylquinoline

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of quinaldine (available from Aldrich) (25 mL, 176 mmol) in trifluoroacetic acid (140 mL) was hydrogenated at 50 psi hydrogen in the presence of PtO2 (2.62 g, 11.5 mmol) for 1.5 h at rt. (This method was conducted in accordance with Bell, T. W. et. al. J. Am. Chem. Soc. 2002 124, 14092 incorporated herein by reference). The mixture was filtered through filter paper, diluted with water and crushed ice, and made basic by the addition of solid NaOH until the mixture was pH>10. The aqueous layer was extracted with hexane. The pooled organic layers were washed with water and dried over MgSO4. The mixture was filtered and evaporated to give 2-methyl-5,6,7,8-tetrahydro-quinoline (Intermediate 200A1) as a clear, yellow oil ˜25 g (98%).

Workup

  1. filtrationThe mixture was filtered
  2. filtrationthrough filter paper
  3. additiondiluted with water
  4. customcrushed ice
  5. additionmade basic by the addition of solid NaOH until the mixture
  6. extractionThe aqueous layer was extracted with hexane
  7. washThe pooled organic layers were washed with water
  8. dry with materialdried over MgSO4
  9. filtrationThe mixture was filtered
  10. customevaporated

Sources & evidence

ORD record
ord-8dcd688dc29c44d490ab6de0b50328dc
Source dataset
uspto-grants-2007_10
Patent number
US07276522B2

Reaction notes

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