Butyl bromide → 4-Benzyloxy-1-butyl-1H-pyridin-2-one

HRID 516618Notes

Reaction equation

HRID 516618 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH3:5].C(=O)([O-])[O-].[K+].[K+].[CH2:12]([O:19][C:20]1[CH:25]=[CH:24][NH:23][C:22](=[O:26])[CH:21]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C(#N)C>[CH2:12]([O:19][C:20]1[CH:25]=[CH:24][N:23]([CH2:2][CH2:3][CH2:4][CH3:5])[C:22](=[O:26])[CH:21]=1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 8002Butyl bromideHCID 11430Potassium CarbonateHCID 36077244-Benzyloxy-2(1H)-pyridone

Product 1

HCID 594970724-Benzyloxy-1-butyl-1H-pyridin-2-oneYield 98%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1-Bromobutane (3.75 g, 27.33 mmol) and potassium carbonate (10.3 g, 74.52 mmol) were added to a solution of 4-benzyloxy-1H-pyridin-2-one (5.0 g, 24.84 mmol) in acetonitrile (200 ml) and the mixture was heated at reflux for 16 hours. The reaction mixture was filtered through diatomaceous earth and concentrated in vacuo. The crude residue was then triturated with diethylether to yield pure D4 (6.26 g, 98%) as a white solid.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 16 hours
  3. filtrationThe reaction mixture was filtered through diatomaceous earth
  4. concentrationconcentrated in vacuo
  5. customThe crude residue was then triturated with diethylether

Sources & evidence

ORD record
ord-6d2732363be24f2d92aaa64ac87e7590
Source dataset
uspto-grants-2015_08
Patent number
US09114138B2

Reaction notes

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