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

HRID 2364940Notes

Reaction equation

HRID 2364940 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>CC#N>[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 CH3CN (200 ml). The mixture was heated at reflux temperature for 16 h. The r.m. was then filtered through diatomaceous earth and concentrated in vacuo. The crude residue was then triturated with diethyl ether to yield pure D1 (6.26 g, 98%) as a white solid.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux temperature for 16 h
  3. filtrationwas then filtered through diatomaceous earth
  4. concentrationconcentrated in vacuo
  5. customThe crude residue was then triturated with diethyl ether

Sources & evidence

ORD record
ord-b63a7ac91c2f4dee95ed745756e50781
Source dataset
uspto-grants-2014_04
Patent number
US08697689B2

Reaction notes

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