Acetone → HCID 70983453, compound

HRID 338971Notes

Reaction equation

HRID 338971 reaction equation
[Br:1][C:2]1[C:3]([OH:13])=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([CH3:12])[CH:8]=[CH:7]2.I[CH:15]([CH3:17])[CH3:16].C(=O)([O-])[O-].[K+].[K+].CC(C)=O>O>[Br:1][C:2]1[C:3]([O:13][CH:15]([CH3:17])[CH3:16])=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([CH3:12])[CH:8]=[CH:7]2

Participants

6

Reactant 4

HCID 180AcetoneHCID 6362Isopropyl iodideHCID 11430Potassium CarbonateHCID 136062505HCID 136062505, compound

Product 1

HCID 70983453HCID 70983453, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 8-bromo-2-methylquinolin-7-ol (0.093 g, 0.39 mmol), 2-iodopropane (0.078 mL, 0.78 mmol) and potassium carbonate (0.16 g, 1.2 mmol) in acetone (1.6 mL, 0.39 mmol) was heated at 70° C. for 12 hours. After cooling, the reaction mixture was diluted with water (10 mL) and extracted with dichloromethane (3×20 mL). The combined organic extracts were dried over magnesium sulfate, filtered and concentrated under reduced pressure. Purification by normal phase chromatography on silica (10% ethyl acetate/hexanes) provided the title compound.

Workup

  1. temperatureAfter cooling
  2. extractionextracted with dichloromethane (3×20 mL)
  3. dry with materialThe combined organic extracts were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customPurification by normal phase chromatography on silica (10% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-86d6f9ae572a4651accb7d454ed85c6f
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

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