Hydrochloric Acid → 2-Chloro-5-iodo-3-nitropyridine

HRID 1434637

Reaktionsgleichung

Reaktionsgleichung von HRID 1434637
[I:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[C:5](N)=[N:6][CH:7]=1.N([O-])=O.[Na+].[NH4+].[OH-].[ClH:18]>Cl[Cu]>[I:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[C:5]([Cl:18])=[N:6][CH:7]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 14923Ammonium HydroxideHCID 33844682-Amino-5-iodo-3-nitropyridineHCID 23668193Sodium Nitrite

Produkt 1

HCID 15142942-Chloro-5-iodo-3-nitropyridineAusbeute 36 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 62652Cuprous chlorideKatalysator

Versuchsvorschrift

5-iodo-3-nitro-2-aminopyridine (2.511 g, 9.48 mmol) and concentrated HCl (20 mL) were stirred at room temperature for ten minutes. Sodium nitrite (13 g, 188 mmol) was then slowly added followed by CuCl (1.0 g, 10 mmol). Stirring continued overnight. The mixture was poured into 1:1 NH4OH:H2O, extracted with ethyl acetate, dried over sodium sulfate, then concentrated. The crude residue was purified by flash chromatography using 9:1 hexane:ethyl acetate to yield 5-iodo-3-nitro-2-chloropyridine (984 mg, 36%) as a colorless solid.

Aufarbeitung

  1. extractionH2O, extracted with ethyl acetate
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated
  4. customThe crude residue was purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-9c8d146798a34822a21c69430887e465
Quelldatensatz
uspto-grants-2009_11
Patentnummer
US07615567B2

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