2-Bromoethanol → 3-(n-Butyl)-4-[2-(2-hydroxyethoxy)ethoxy]-1-phenyl-1,8-naphthyridin-2(1H)one

HRID 1583316Notes

Reaction equation

HRID 1583316 reaction equation
[CH2:1]([C:5]1[C:6](=[O:25])[N:7]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:8]2[C:13]([C:14]=1[O:15][CH2:16][CH2:17][OH:18])=[CH:12][CH:11]=[CH:10][N:9]=2)[CH2:2][CH2:3][CH3:4].[H-].[Na+].Br[CH2:29][CH2:30][OH:31]>O1CCOCC1>[CH2:1]([C:5]1[C:6](=[O:25])[N:7]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:8]2[C:13]([C:14]=1[O:15][CH2:16][CH2:17][O:18][CH2:29][CH2:30][OH:31])=[CH:12][CH:11]=[CH:10][N:9]=2)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 108982-BromoethanolHCID 24758Sodium hydrideHCID 133709283-Butyl-4-(2-hydroxyethoxy)-1-phenyl-1,8-naphthyridin-2(1H)-one

Product 1

HCID 202016933-(n-Butyl)-4-[2-(2-hydroxyethoxy)ethoxy]-1-phenyl-1,8-naphthyridin-2(1H)one

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a mixture of 6.8 g of 3-(n-butyl)-4-(2-hydroxyethoxy)-1-phenyl-1,8-naphthyridin-2(1H)one and 150 ml of anhydrous dioxane there is added 0.8 g of sodium hydride (60% oil dispersion) with stirring. The reaction mixture is stirred and warmed on a steam bath for 30 minutes, followed by the dropwise addition of 2.6 g of 95% 2-bromoethanol. The reaction mixture is stirred and refluxed for 24 hours, the solvent is removed in vacuo and the residual solid is dissolved in chloroform. The chloroform solution is successively washed with water, 0.5N sodium hydroxide and water. The organic layer is dried over magnesium sulfate, filtered and concentrated to dryness to yield the product of this example.

Workup

  1. stirringThe reaction mixture is stirred
  2. temperaturewarmed on a steam bath for 30 minutes
  3. stirringThe reaction mixture is stirred
  4. temperaturerefluxed for 24 hours
  5. customthe solvent is removed in vacuo
  6. dissolutionthe residual solid is dissolved in chloroform
  7. washThe chloroform solution is successively washed with water, 0.5N sodium hydroxide and water
  8. dry with materialThe organic layer is dried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated to dryness
  11. customto yield the product of this example

Sources & evidence

ORD record
ord-16c281a8283e4f659202dca6e9ab0702
Source dataset
uspto-grants-1985_11
Patent number
US04551463

Reaction notes

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