Hydrochloric Acid → 2-Azido-6-chloropyridine

HRID 386054

Reaktionsgleichung

Reaktionsgleichung von HRID 386054
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([NH:8][NH2:9])[N:3]=1.Cl.[N:11]([O-])=O.[Na+]>O>[N:8]([C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[N:3]=1)=[N+:9]=[N-:11]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 3200042-Chloro-6-hydrazinopyridineHCID 23668193Sodium Nitrite

Produkt 1

HCID 215763792-Azido-6-chloropyridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

2-Chloro-6-hydrazinopyridine (3.00 g, 20.90 mmol) was suspended in water (20 mL) and cooled to 0° C. Concentrated HCl (3.00 mL, 36.5 mmol) was added to dissolve the starting material and attain a pH of ˜1. Sodium nitrite (1.73 g, 25.07 mmol) in water (10 mL) was added dropwise. The thick suspension was allowed to warm to room temperature and extracted with CH2Cl2 (2×). The combined organic layers were dried (MgSO4), filtered, and evaporated. The crude residue was purified by flash chromatography (0-10% EtOAc/hexanes) to afford the title compound as a colorless solid.

Aufarbeitung

  1. dissolutionto dissolve the starting material
  2. temperatureto warm to room temperature
  3. extractionextracted with CH2Cl2 (2×)
  4. dry with materialThe combined organic layers were dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude residue was purified by flash chromatography (0-10% EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-18c8d642221240debf16412ecc5d6397
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08367706B2

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