Sodium Azide → HCID 23369752, compound

HRID 1900862Notes

Reaction equation

HRID 1900862 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[CH2:17][CH:16]([CH2:18]Br)[O:15][C:5]2=[C:6]2[C:11]=1[NH:10][C:9](=[O:12])[CH2:8][C:7]2([CH3:14])[CH3:13].[N-:20]=[N+:21]=[N-:22].[Na+]>CN(C)C=O>[N:20]([CH2:18][CH:16]1[O:15][C:5]2=[C:6]3[C:11](=[C:2]([Br:1])[CH:3]=[C:4]2[CH2:17]1)[NH:10][C:9](=[O:12])[CH2:8][C:7]3([CH3:14])[CH3:13])=[N+:21]=[N-:22]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 23369748HCID 23369748, compound

Product 1

HCID 23369752HCID 23369752, compoundYield 88.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-Bromo-2-bromomethyl-9,9-dimethyl-2,3,6,7,8,9-hexahydrofuro[2,3-f]quinoline-7-one (1.25 g, 3.21 mmol) was dissolved in dimethylformamide (50 ml). To the resultant solution, sodium azide (1.25 g, 19.3 mmol) was added, and the mixture was stirred at room temperature for 17 hours. The reaction mixture was condensed under reduced pressure, and the residue was extracted along with chloroform and water. The organic phase was dried, and condensed under reduced pressure. Recrystallization from chloroform-n-hexane-ether yielded 997 mg of the title compound as pale yellow needles (88.4%).

Workup

  1. customcondensed under reduced pressure
  2. extractionthe residue was extracted along with chloroform and water
  3. customThe organic phase was dried
  4. customcondensed under reduced pressure
  5. customRecrystallization from chloroform-n-hexane-ether

Sources & evidence

ORD record
ord-f65f33a63ef74d7f958bf56476d85ade
Source dataset
uspto-grants-1996_11
Patent number
US05576324

Reaction notes

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