Water → 7-Isopropoxy-2,8-dimethylquinoline

HRID 338920Notes

Reaction equation

HRID 338920 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[C:5]([CH3:13])[C:6]([OH:12])=[CH:7][CH:8]=2)[N:3]=1.I[CH:15]([CH3:17])[CH3:16].C(=O)([O-])[O-].[K+].[K+].O>CC(C)=O>[CH:15]([O:12][C:6]1[C:5]([CH3:13])=[C:4]2[C:9]([CH:10]=[CH:11][C:2]([CH3:1])=[N:3]2)=[CH:8][CH:7]=1)([CH3:17])[CH3:16]

Participants

6

Reactant 4

HCID 962WaterHCID 6362Isopropyl iodideHCID 11430Potassium CarbonateHCID 1357421682,8-Dimethylquinolin-7-ol

Product 1

HCID 709835887-Isopropoxy-2,8-dimethylquinolineYield 24.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2,8-Dimethylquinolin-7-ol (1.0 g, 2.31 mmol), 2-iodopropane (0.785 g, 4.62 mmol) and potassium carbonate (0.957 g, 6.93 mmol) in acetone (15 mL) were heated to 70° C. in a sealed tube for 18 hours. After cooling, water (20 mL) was added and the aqueous phase was extracted with DCM. The combined organic phases were dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified by reverse phase chromatography (SP4, 25M, eluting with a gradient of water/ACN 100:0 to 0:100, 20 column volumes) to yield 7-isopropoxy-2,8-dimethylquinoline (120 mg, 24.1% yield) as an oil

Workup

  1. temperatureAfter cooling
  2. extractionthe aqueous phase was extracted with DCM
  3. dry with materialThe combined organic phases were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by reverse phase chromatography (SP4, 25M
  7. washeluting with a gradient of water/ACN 100:0 to 0:100, 20 column volumes)

Sources & evidence

ORD record
ord-7134883adfa64f768a3de8045ca6f0c2
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

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