2-Phenylquinoline → 2-Phenyl-5,6,7,8-tetrahydroquinoline

HRID 353361

Reaction equation

HRID 353361 reaction equation
[C:1]1([C:7]2[CH:16]=[CH:15][C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>C(O)(C(F)(F)F)=O.O=[Pt]=O>[C:1]1([C:7]2[CH:16]=[CH:15][C:14]3[CH2:13][CH2:12][CH2:11][CH2:10][C:9]=3[N:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 1

HCID 715452-Phenylquinoline

Product 1

HCID 111383402-Phenyl-5,6,7,8-tetrahydroquinolineYield 80%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
60 °C

Procedure

To a vigorously stirred solution of 2-phenylquinoline (6.0 g, 29 mmol) in TFA (30 mL) in a 250 mL round-bottomed flask under nitrogen was added PtO2 (332 mg, 1.5 mmol) in one portion. The resulting mixture was then placed under a hydrogen atmosphere (H2 flush for 5 min, then H2 balloon with a wide-bore needle) and heated to 60° C. Stirring was continued for 5 h, at which time GLC analysis indicated all of the starting material was consumed. The reaction was cooled to room temperature and the TFA was evaporated in vacuo. The residue was rendered basic with a minimum amount of 4 N NaOH and extracted with CHCl3 (3×50 mL), dried (MgSO4) and concentrated in vacuo. Purification of the residue by flash chromatography (silica gel, hexane/EtOAc 10:1) afforded 4.85 g of 2-phenyl-5,6,7,8-tetrahydroquinoline (80% yield).

Workup

  1. customflush for 5 min
  2. customwas consumed
  3. temperatureThe reaction was cooled to room temperature
  4. customthe TFA was evaporated in vacuo
  5. extractionextracted with CHCl3 (3×50 mL)
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. customPurification of the residue by flash chromatography (silica gel, hexane/EtOAc 10:1)

Sources & evidence

ORD record
ord-c9161476414241ccbbedf7c9f85dc7f2
Source dataset
uspto-grants-2004_06
Patent number
US06750348B1

Linked notes

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