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

HRID 338999

反応式

HRID 338999 の反応式
[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

参加物

6

反応物 2

HCID 31398ChlorosuccinimideHCID 1354519692-Methylquinolin-7-ol

生成物 1

HCID 1358589748-Chloro-2-methylquinolin-7-ol収率 55.1%

試薬・触媒・溶媒 3

HCID 9856075Zirconium chloride (ZrCl4), (T-4)-触媒HCID 6212Chloroform溶媒HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-b3b18598e8a749c38eb447892a2ab23c
出典データセット
uspto-grants-2014_11
特許番号
US08889704B2

関連ノート

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