Sodium Azide → HCID 23369851, compound

HRID 1900789Notes

Reaction equation

HRID 1900789 reaction equation
Br[CH2:2][CH:3]1[O:19][C:6]2=[C:7]3[C:12](=[C:13]([CH3:15])[CH:14]=[C:5]2[CH2:4]1)[NH:11][C:10](=[O:16])[C:9]([CH3:17])=[C:8]3[CH3:18].[N-:20]=[N+:21]=[N-:22].[Na+]>CN(C)C=O>[N:20]([CH2:2][CH:3]1[O:19][C:6]2=[C:7]3[C:12](=[C:13]([CH3:15])[CH:14]=[C:5]2[CH2:4]1)[NH:11][C:10](=[O:16])[C:9]([CH3:17])=[C:8]3[CH3:18])=[N+:21]=[N-:22]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 23369697HCID 23369697, compound

Product 1

HCID 23369851HCID 23369851, compoundYield 95.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Bromomethyl-5,8,9-trimethyl-2,3,6,7-tetrahydrofuro-[2,3-f]quinoline-7-one (1.07 g, 3.32 mmol) was dissolved in N,N-dimethylformamide (30 ml). To the obtained solution, sodium azide (1.29 g, 19.9 mmol) was added. The mixture was stirred at room temperature for 4 hours. The reaction mixture was subjected to distillation under reduced pressure for removing the solvent. To the resultant residue, chloroform and water were added. The mixture was extracted, dried, and condensed. Recrystallization from chloroform--n-hexane yielded 8.99 mg of the title compound as yellow needles (95.2%).

Workup

  1. distillationThe reaction mixture was subjected to distillation under reduced pressure
  2. customfor removing the solvent
  3. additionTo the resultant residue, chloroform and water were added
  4. extractionThe mixture was extracted
  5. customdried
  6. customcondensed
  7. customRecrystallization from chloroform

Sources & evidence

ORD record
ord-3d69ea725a86488cbeaa45976c9eb6a1
Source dataset
uspto-grants-1996_11
Patent number
US05576324

Reaction notes

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