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

HRID 338999Notes

Reaction equation

HRID 338999 reaction equation
[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

Participants

6

Reactant 2

HCID 31398ChlorosuccinimideHCID 1354519692-Methylquinolin-7-ol

Product 1

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

Reagents, catalysts & solvents 3

HCID 9856075Zirconium chloride (ZrCl4), (T-4)-CatalystHCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-b3b18598e8a749c38eb447892a2ab23c
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

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