Sodium Azide → 4-Azido-8-fluoroquinoline

HRID 1608945Notes

Reaction equation

HRID 1608945 reaction equation
Cl[C:2]1[C:11]2[C:6](=[C:7]([F:12])[CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1.[N-:13]=[N+:14]=[N-:15].[Na+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.ClCCl.O>[N:13]([C:2]1[C:11]2[C:6](=[C:7]([F:12])[CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1)=[N+:14]=[N-:15]

Participants

6

Reactant 2

HCID 33557Sodium AzideHCID 27365874-Chloro-8-fluoroquinoline

Product 1

HCID 157905214-Azido-8-fluoroquinolineYield 93.2%

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 2.08 g (0.0114 mol) of 4-chloro-8-fluoroquinoline, 1.12 g (0.0172 mol) of sodium azide, and 4.10 g ((0.0127 mol) of tetrabutyl ammonium bromide in 70 mL of dichloromethane and 25 mL of water was refluxed overnight. The layers were then separated and the organic layer was washed once with water, passed through phase separating paper, and concentrated to an oil, which was triturated with ether. The solid was filtered and the filtrate was concentrated to give 2.0 g of the title product.

Workup

  1. temperaturewas refluxed overnight
  2. customThe layers were then separated
  3. washthe organic layer was washed once with water
  4. customseparating paper
  5. concentrationconcentrated to an oil, which
  6. customwas triturated with ether
  7. filtrationThe solid was filtered
  8. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-3805dc81c5b84335906284d79a14f4e1
Source dataset
uspto-grants-1995_03
Patent number
US05399564

Reaction notes

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