Benzyl Bromide → 8-Benzyloxy-3-methyl-1H-quinolin-2-one

HRID 1815068Notes

Reaction equation

HRID 1815068 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[OH:15][C:16]1[CH:17]=[CH:18][CH:19]=[C:20]2[C:25]=1[NH:24][C:23](=[O:26])[C:22]([CH3:27])=[CH:21]2>CC(C)=O>[CH2:1]([O:15][C:16]1[CH:17]=[CH:18][CH:19]=[C:20]2[C:25]=1[NH:24][C:23](=[O:26])[C:22]([CH3:27])=[CH:21]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 4409863-Methyl-quinolin-2,8-diol

Product 1

HCID 224992238-Benzyloxy-3-methyl-1H-quinolin-2-one

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Benzyl bromide (1.28 mL) is added to a suspension of potassium carbonate (2.98 g) in a solution of 8-hydroxy-3-methyl-1H-quinolin-2-one (1.26 g) in acetone (36 mL) at room temperature. The reaction mixture is refluxed for 18 hours, filtered, evaporated and purified by flash column chromatography on silica gel, eluting with 2% methanol in dichloromethane.

Workup

  1. temperatureThe reaction mixture is refluxed for 18 hours
  2. filtrationfiltered
  3. customevaporated
  4. custompurified by flash column chromatography on silica gel
  5. washeluting with 2% methanol in dichloromethane

Sources & evidence

ORD record
ord-6de3271194a543b593fef97fd897e5e8
Source dataset
uspto-grants-2005_04
Patent number
US06878721B1

Reaction notes

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