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

HRID 1248951Notes

Reaction equation

HRID 1248951 reaction equation
[CH2:1]([C:5]1[C:6](=[O:22])[N:7]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:8]2[C:13]([C:14]=1[OH:15])=[CH:12][CH:11]=[CH:10][N:9]=2)[CH2:2][CH2:3][CH3:4].C(=O)([O-])[O-].[K+].[K+].Br[CH2:30][CH2:31][OH:32]>CC(C)=O>[CH2:1]([C:5]1[C:6](=[O:22])[N:7]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:8]2[C:13]([C:14]=1[O:15][CH2:30][CH2:31][OH:32])=[CH:12][CH:11]=[CH:10][N:9]=2)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 108982-BromoethanolHCID 11430Potassium CarbonateHCID 54704755Sch 12223

Product 1

HCID 133709283-Butyl-4-(2-hydroxyethoxy)-1-phenyl-1,8-naphthyridin-2(1H)-oneYield 58.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Reflux a stirred solution of 16.2 gm of 3-(n-butyl)-4-hydroxy-1-phenyl-1,8-naphthyridin-2(1H)one and 11.4 gm of anhydrous potassium carbonate powder in 600 ml of dry acetone for 30 minutes. 95% 2-bromoethanol (10.3 gm) is added dropwise to the solution. The reaction is refluxed for 26 hours, cooled and the solvent removed by stripping. The resulting solid is dissolved in 500 ml chloroform and the chloroform solution is washed with 300 ml water, twice with 100 ml of 0.5N sodium hydroxide solution and finally with 100 ml of water. The chloroform solution is dried over magnesium sulfate, filtered and the solvent is removed to give the crude product. The crude product is triturated with warm isopropyl ether to give 10.9 gm of the 3-(n-butyl)-4-(2-hydroxyethoxy)-1-phenyl-1,8-naphthyridin-2(1H)one; which after recrystallization from acetone melts at 138°-140° C.

Workup

  1. temperatureThe reaction is refluxed for 26 hours
  2. temperaturecooled
  3. customthe solvent removed
  4. dissolutionThe resulting solid is dissolved in 500 ml chloroform
  5. washthe chloroform solution is washed with 300 ml water, twice with 100 ml of 0.5N sodium hydroxide solution and finally with 100 ml of water
  6. dry with materialThe chloroform solution is dried over magnesium sulfate
  7. filtrationfiltered
  8. customthe solvent is removed
  9. customto give the crude product
  10. customThe crude product is triturated with warm isopropyl ether

Sources & evidence

ORD record
ord-3548ad3df99b46ebbf465b9e3e75ee2f
Source dataset
uspto-grants-1986_12
Patent number
US04628055

Reaction notes

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