Water → 3-(benzyloxy)-5-bromo-1-methylpyridin-2(1H)-one

HRID 625932Notes

Reaction equation

HRID 625932 reaction equation
[CH2:1]([O:8][C:9]1[C:10](=[O:16])[NH:11][CH:12]=[C:13]([Br:15])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:17]([O-])([O-])=O.[K+].[K+].IC.O>CN(C=O)C>[CH2:1]([O:8][C:9]1[C:10](=[O:16])[N:11]([CH3:17])[CH:12]=[C:13]([Br:15])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 674068463-(benzyloxy)-5-bromopyridin-2(1H)-one

Product 1

HCID 674178603-(benzyloxy)-5-bromo-1-methylpyridin-2(1H)-oneYield 87.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 2.51 g (8.96 mmol) 3-benzyloxy-5-bromo-1H-pyridin-2-one and 2.48 g (17.9 mmol) K2CO3 in 45 mL DMF was added 1.12 mL (17.9 mmol) iodomethane at room temperature. After stirring overnight, 150 mL water was added with vigorous stirring causing precipitation of the product which was collected by filtration and dried in vacuo affording 2.3 g (87%) 3-benzyloxy-5-bromo-1-methyl-1H-pyridin-2-one

Workup

  1. stirringwith vigorous stirring
  2. customprecipitation of the product which
  3. filtrationwas collected by filtration
  4. customdried in vacuo

Sources & evidence

ORD record
ord-6dc501ab7a7043bba1f71557da576b5b
Source dataset
uspto-grants-2016_04
Patent number
US09309199B2

Reaction notes

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