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

HRID 353361

반응식

HRID 353361 반응식
[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

참가 물질

4

반응물 1

HCID 715452-Phenylquinoline

생성물 1

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

시약·촉매·용매 2

HCID 345198Adams' catalyst촉매HCID 6422Trifluoroacetic acid용매

반응 조건

온도
60 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-c9161476414241ccbbedf7c9f85dc7f2
출처 데이터셋
uspto-grants-2004_06
특허 번호
US06750348B1

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