Water → 6-Fluoro-8-isopropoxy-2-methylquinoline

HRID 338886Notes

Reaction equation

HRID 338886 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([OH:12])[CH:11]=1)[N:8]=[C:7]([CH3:13])[CH:6]=[CH:5]2.I[CH:15]([CH3:17])[CH3:16].C([O-])([O-])=O.[K+].[K+].O>CC(C)=O>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([O:12][CH:15]([CH3:17])[CH3:16])[CH:11]=1)[N:8]=[C:7]([CH3:13])[CH:6]=[CH:5]2

Participants

6

Reactant 4

HCID 962WaterHCID 6362Isopropyl iodideHCID 11430Potassium CarbonateHCID 667815176-Fluoro-8-hydroxy-2-methylquinoline

Product 1

HCID 709829066-Fluoro-8-isopropoxy-2-methylquinolineYield 89.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
70 °C

Procedure

To 6-fluoro-2-methylquinolin-8-ol (1.0 g, 5.6 mmol) in acetone (20 mL) were added 2-iodopropane (1.9 g, 11 mmol) and K2CO3 (2.3 g, 17 mmol). The reaction was heated to 70° C. for 20 hours in a sealed tube and then cooled. Water was added and the aqueous phase was extracted with DCM. The combined organic phases were washed with brine, dried with MgSO4, filtered and concentrated under reduced pressure to yield 6-fluoro-8-isopropoxy-2-methylquinoline (1.1 g, 89% yield) as a dark oil.

Workup

  1. temperaturecooled
  2. extractionthe aqueous phase was extracted with DCM
  3. washThe combined organic phases were washed with brine
  4. dry with materialdried with MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5e47305a34dd40129b9ecefc5f571bc5
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

Loading…