Allyl bromide → 1,6-Naphthyridine, 5,6,7,8-tetrahydro-6-(2-propenyl)-

HRID 1660496Notes

Reaction equation

HRID 1660496 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][N:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[CH2:11](Br)[CH:12]=[CH2:13].[BH4-].[Na+]>CC(C)=O.CO>[CH2:13]([N:7]1[CH2:8][CH2:9][C:10]2[N:1]=[CH:2][CH:3]=[CH:4][C:5]=2[CH2:6]1)[CH:12]=[CH2:11]

Participants

6

Reactant 3

HCID 7841Allyl bromideHCID 674881,6-NaphthyridineHCID 4311764Sodium borohydride

Product 1

HCID 30586941,6-Naphthyridine, 5,6,7,8-tetrahydro-6-(2-propenyl)-

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 887MethanolSolvent

Procedure

A solution of 1,6-naphthyridine (6.5 g, 0.05 mol) and allyl bromide (9.1 g, 0.075 mol) in acetone (50 ml) was refluxed for 8 hours. The precipitated quatenary salt was separated by filtration, dissolved in technical grade methanol (300 ml) and sodium borohydride (18.9 g, 0.5 mol) was added portionwise under ice cooling. After stirring overnight at room temperature, the reaction mixture was evaporated in vacuo, water added and extracted with benzene. The benzene layer was dried over anhydrous potassium carbonate and evaporated in vacuo. The residue was purified by alumina column chromatography (eluted successively with n-hexane and benzene-chloroform (3:1)) and distilled, bp 98° C./1.0 mmHg, to afford the Compound No. 12 (5.70 g, 65.5%) as a colorless oil.

Workup

  1. customThe precipitated quatenary salt was separated by filtration
  2. additionwas added portionwise under ice cooling
  3. customthe reaction mixture was evaporated in vacuo, water
  4. additionadded
  5. extractionextracted with benzene
  6. dry with materialThe benzene layer was dried over anhydrous potassium carbonate
  7. customevaporated in vacuo
  8. customThe residue was purified by alumina column chromatography (
  9. washeluted successively with n-hexane and benzene-chloroform (3:1)) and
  10. distillationdistilled
  11. custombp 98° C./1.0 mmHg, to afford the Compound No

Sources & evidence

ORD record
ord-8e01d143f99b45d19febe21f4845e04b
Source dataset
uspto-grants-1981_12
Patent number
US04308273

Reaction notes

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