Isopropyl iodide → 6-Fluoro-7-isopropoxy-2-methylquinoline

HRID 338930Notes

Reaction equation

HRID 338930 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[OH:12])[N:8]=[C:7]([CH3:13])[CH:6]=[CH:5]2.I[CH:15]([CH3:17])[CH3:16].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O.O>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][CH:15]([CH3:17])[CH3:16])[N:8]=[C:7]([CH3:13])[CH:6]=[CH:5]2

Participants

6

Reactant 3

HCID 6362Isopropyl iodideHCID 11430Potassium CarbonateHCID 1363380756-Fluoro-2-methylquinolin-7-ol

Product 1

HCID 709833366-Fluoro-7-isopropoxy-2-methylquinolineYield 39%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

To 6-fluoro-2-methylquinolin-7-ol (800 mg, 3.16 mmol) in acetone (5 mL) were added 2-iodopropane (1075 mg, 6.32 mmol) and potassium carbonate (1310 mg, 9.48 mmol). The reaction was stirred at 70° C. in a sealed tube for 18 hours then cooled and diluted with water. The aqueous phase was extracted with DCM, dried over MgSO4, filtered and concentrated under reduced pressure to yield 6-fluoro-7-isopropoxy-2-methylquinoline (270 mg, 39.0% yield) as an oil.

Workup

  1. temperaturethen cooled
  2. extractionThe aqueous phase was extracted with DCM
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-23ccd53618ec41b2bfafb4de575361ab
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

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