Chlorosuccinimide → 8-Chloro-2-methylquinolin-7-ol

HRID 338999

반응식

HRID 338999 반응식
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][C:6]([OH:12])=[CH:7][CH:8]=2)[N:3]=1.[Cl:13]N1C(=O)CCC1=O>C(Cl)Cl.C(Cl)(Cl)Cl.[Cl-].[Zr+4].[Cl-].[Cl-].[Cl-]>[Cl:13][C:5]1[C:6]([OH:12])=[CH:7][CH:8]=[C:9]2[C:4]=1[N:3]=[C:2]([CH3:1])[CH:11]=[CH:10]2

참가 물질

6

반응물 2

HCID 31398ChlorosuccinimideHCID 1354519692-Methylquinolin-7-ol

생성물 1

HCID 1358589748-Chloro-2-methylquinolin-7-ol수율 55.1%

시약·촉매·용매 3

HCID 9856075Zirconium chloride (ZrCl4), (T-4)-촉매HCID 6212Chloroform용매HCID 6344Dichloromethane용매

실험 절차

2-Methylquinolin-7-ol (200 mg, 1.26 mmol) was added to a solution of 1-chloropyrrolidine-2,5-dione (168 mg, 1.26 mmol) and zirconium(IV) chloride (14.6 mg, 0.0628 mmol) in DCM (10 mL) and the reaction was stirred at ambient temperature for 24 hours. The reaction was diluted with chloroform (30 mL) and washed with an aqueous sodium carbonate solution followed by brine. After drying (MgSO4), the solution was filtered and concentrated under reduced pressure and the residue was purified by reverse phase chromatography (SP4, 25 M, eluting with a gradient of water/ACN 90:10 to 0:100, 30 column volumes) to yield 8-chloro-2-methylquinolin-7-ol (134 mg, 55.1% yield) as a thick oil.

후처리

  1. washwashed with an aqueous sodium carbonate solution
  2. dry with materialAfter drying (MgSO4)
  3. filtrationthe solution was filtered
  4. concentrationconcentrated under reduced pressure
  5. customthe residue was purified by reverse phase chromatography (SP4, 25 M
  6. washeluting with a gradient of water/ACN 90:10 to 0:100, 30 column volumes)

출처 및 근거

ORD 기록
ord-b3b18598e8a749c38eb447892a2ab23c
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08889704B2

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