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

HRID 353361

反応式

HRID 353361 の反応式
[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

参加物

4

反応物 1

HCID 715452-Phenylquinoline

生成物 1

HCID 111383402-Phenyl-5,6,7,8-tetrahydroquinoline収率 80%

試薬・触媒・溶媒 2

HCID 345198Adams' catalyst触媒HCID 6422Trifluoroacetic acid溶媒

反応条件

温度
60 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-c9161476414241ccbbedf7c9f85dc7f2
出典データセット
uspto-grants-2004_06
特許番号
US06750348B1

関連ノート

読み込み中…