Benzyl Bromide → 1-[8-(Benzyloxy)quinolin-5-yl]ethan-1-one

HRID 883626Notes

Reaction equation

HRID 883626 reaction equation
[C:1]([C:4]1[CH:13]=[CH:12][C:11]([OH:14])=[C:10]2[C:5]=1[CH:6]=[CH:7][CH:8]=[N:9]2)(=[O:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH2:21](Br)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>CC(C)=O>[C:1]([C:4]1[CH:13]=[CH:12][C:11]([O:14][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[C:10]2[C:5]=1[CH:6]=[CH:7][CH:8]=[N:9]2)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 95877Quinacetol

Product 1

HCID 137448911-[8-(Benzyloxy)quinolin-5-yl]ethan-1-one

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
50 °C

Procedure

A 5 liter 4-necked flask equipped with a mechanical stirrer, thermometer, addition funnel and refluxing condenser was charged with 5-acetyl-8-hydroxyquinoline (300 gms/1.44 moles) and acetone (3 liters). To this solution was added anhydrous potassium carbonate (443 gms/1.6 moles) in 30 minutes followed by benzyl bromide (229 ml/1.92 moles) slowly in 90 minutes. The resulting slurry was heated to reflux for 12 hours. The reaction mass was filtered through hyflo bed, after completion of reaction and washed with hot ethyl acetate (300 ml). The clear filtrate was distilled out completely at 55-60° C. under high vacuum. The residue was dissolved in acetone (300 ml) and warmed to 50° C. for 5-10 minutes, cooled to 25-30° C., chilled further to 0-5° C. and stirred for 30 minutes. The resulting 5-Acetyl-8-benzyloxyquinoline was isolated by filtration and washed with 1:1 mixture of acetone and diisopropyl ether (150 ml) and dried under vacuum at 60-65° C. for 4-5 hours. Yield-202 gms.

Workup

  1. customA 5 liter 4-necked flask equipped with a mechanical stirrer
  2. additionthermometer, addition funnel
  3. temperaturerefluxing condenser
  4. temperatureThe resulting slurry was heated
  5. temperatureto reflux for 12 hours
  6. filtrationThe reaction mass was filtered through hyflo bed
  7. customafter completion of reaction
  8. washwashed with hot ethyl acetate (300 ml)
  9. distillationThe clear filtrate was distilled out completely at 55-60° C. under high vacuum
  10. dissolutionThe residue was dissolved in acetone (300 ml)
  11. temperaturecooled to 25-30° C.
  12. temperaturechilled further to 0-5° C.

Sources & evidence

ORD record
ord-e18b3183645f400288a63356f7b4b961
Source dataset
uspto-grants-2012_08
Patent number
US08236959B2

Reaction notes

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