Acetone → HCID 70983851, compound

HRID 339029Notes

Reaction equation

HRID 339029 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[C:5]([OH:12])[CH:6]=[CH:7][CH:8]=2)[N:3]=1.[C:13]([O:16][CH2:17][CH2:18]Br)(=[O:15])[CH3:14].C(=O)([O-])[O-].[K+].[K+].CC(C)=O>O>[C:13]([O:16][CH2:17][CH2:18][O:12][C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:4]=1[N:3]=[C:2]([CH3:1])[CH:11]=[CH:10]2)(=[O:15])[CH3:14]

Participants

6

Reactant 4

HCID 180AcetoneHCID 11430Potassium CarbonateHCID 132242-Methyl-8-hydroxyquinolineHCID 135641-Acetoxy-2-bromoethane

Product 1

HCID 70983851HCID 70983851, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 2-methylquinolin-8-ol (0.30 g, 1.9 mmol), 2-bromoethyl acetate (0.8.2 mL, 7.6 mmol) and potassium carbonate (1.6 g, 12 mmol) in acetone (7.5 mL, 1.9 mmol) was heated at 70° C. for 12 hours. The cooled 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. The residue was purified by reverse phase chromatography on a C18 column (0-100% acetonitrile/water) to provide the title compound (0.29 g, 63%).

Workup

  1. customThe cooled reaction mixture
  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. customThe residue was purified by reverse phase chromatography on a C18 column (0-100% acetonitrile/water)

Sources & evidence

ORD record
ord-444cd86c040a42d8b80714ad51c58f15
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

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