Allyl bromide → 1,8-Naphthyridin-2(1H)-one, 1-phenyl-4-(2-propenyloxy)-

HRID 1982398Notes

Reaction equation

HRID 1982398 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[N:7][CH:8]=[CH:9][CH:10]=2)[N:5]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:4](=[O:18])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:25](Br)[CH:26]=[CH2:27]>CC(C)=O>[C:12]1([N:5]2[C:6]3[C:11](=[CH:10][CH:9]=[CH:8][N:7]=3)[C:2]([O:1][CH2:27][CH:26]=[CH2:25])=[CH:3][C:4]2=[O:18])[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 546864734-Hydroxy-1-phenyl-1,8-naphthyridin-2(1H)-one

Product 1

HCID 116591521,8-Naphthyridin-2(1H)-one, 1-phenyl-4-(2-propenyloxy)-

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a mixture of 62 g. of 4-hydroxy-1-phenyl-1,8-naphthyridin-2(1H)-one, 39.6 g. of anhydrous potassium carbonate and 1,800 ml of acetone, there is added dropwise, with stirring, 37.5 g. of allyl bromide. The reaction mixture is refluxed for 22 hours, concentrated in vacuo, and the residue extracted with 600 ml. of chloroform. The organic extract is washed with water, 1N sodium hydroxide solution and again with water, dried over anhydrous magnesium sulfate, filtered and concentrated. The crude solid is triturated with 3×400 ml of boiling isopropyl ether and filtered, yielding the insoluble product, wt. 38.5 g., m.p. 171°-174°. Recrystallization from methanol produces the product as a colorless solid, m.p. 176°-177° C.

Workup

  1. additionTo a mixture of 62 g
  2. temperatureThe reaction mixture is refluxed for 22 hours
  3. concentrationconcentrated in vacuo
  4. extractionthe residue extracted with 600 ml
  5. extractionThe organic extract
  6. washis washed with water, 1N sodium hydroxide solution and again with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe crude solid is triturated with 3×400 ml of boiling isopropyl ether
  11. filtrationfiltered
  12. customyielding the insoluble product, wt. 38.5 g
  13. customRecrystallization from methanol

Sources & evidence

ORD record
ord-7b1fb4bd723f4410999a2e07c5270487
Source dataset
uspto-grants-1986_06
Patent number
US04596809

Reaction notes

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