5(6H)-Quinolinone, 7,8-dihydro- → 5,6,7,8-Tetrahydroquinolin-5-ol

HRID 1292050

반응식

HRID 1292050 반응식
[N:1]1[C:10]2[CH2:9][CH2:8][CH2:7][C:6](=[O:11])[C:5]=2[CH:4]=[CH:3][CH:2]=1.[BH4-].[Na+]>CO>[OH:11][CH:6]1[CH2:7][CH2:8][CH2:9][C:10]2[N:1]=[CH:2][CH:3]=[CH:4][C:5]1=2

참가 물질

4

반응물 2

HCID 30168115(6H)-Quinolinone, 7,8-dihydro-HCID 4311764Sodium borohydride

생성물 1

HCID 45989235,6,7,8-Tetrahydroquinolin-5-ol

시약·촉매·용매 1

HCID 887Methanol용매

반응 조건

온도
0 °C

실험 절차

5,6,7,8-Tetrahydro-5-quinolinone, synthesized according to the literature procedure by F. Zymalkowski and H. Rimek, Arch. Pharm. (1961) volume 294, pp. 759-765, (10.0 g, 67.9 mol) was dissolved in MeOH (350 mL) and cooled to 0° C. under an atmosphere of nitrogen. To the solution was added NaBH4 (7.7 g, 0.204 mol) portionwise over 60 minutes. The reaction was stirred at ambient temperature for 24 h. The mixture was concentrated under reduced pressure and partitioned between EtOAc (600 mL) and saturated aqueous NaHCO3 (250 mL). The EtOAc layer was dried (MgSO4), filtered, and the solvent was removed under reduced presssure. The residue was purified by pressurized silica gel column chromatography using 97:3 CH2Cl2 :MeOH as eluant. 5-Hydroxy 5,6,7,8-tetrahydro-quinoline was obtained as a pale yellow solid (TLC Rf = 0.14 (98:2 CH2Cl2 :MeOH)).

후처리

  1. concentrationThe mixture was concentrated under reduced pressure
  2. custompartitioned between EtOAc (600 mL) and saturated aqueous NaHCO3 (250 mL)
  3. dry with materialThe EtOAc layer was dried (MgSO4)
  4. filtrationfiltered
  5. customthe solvent was removed
  6. customThe residue was purified by pressurized silica gel column chromatography

출처 및 근거

ORD 기록
ord-65ec729d14e94dbe936c523e8c4a78c2
출처 데이터셋
uspto-grants-1998_05
특허 번호
US05756497

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