Sodium Azide → 4-Azido-8-fluoroquinoline

HRID 235047

Reaktionsgleichung

Reaktionsgleichung von HRID 235047
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]

Komponenten

6

Edukt 2

HCID 33557Sodium AzideHCID 27365874-Chloro-8-fluoroquinoline

Produkt 1

HCID 157905214-Azido-8-fluoroquinolineAusbeute 93,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 74236Tetrabutylammonium BromideKatalysatorHCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-276fd8bdc9a64e789f514668a6ca3727
Quelldatensatz
uspto-grants-1997_01
Patentnummer
US05597836

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