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

HRID 577625Notes

Reaction equation

HRID 577625 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, during 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, during with 2% methanol in dichloromethane

Sources & evidence

ORD record
ord-28d21dc6f12544109bb9939ca5c4aafe
Source dataset
uspto-grants-2015_05
Patent number
US09040559B2

Reaction notes

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