Nitric Acid → 4-Chloro-3-nitropyridin-2-amine

HRID 447663

Reaktionsgleichung

Reaktionsgleichung von HRID 447663
[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][N:3]=1.[N+:9]([O-])([OH:11])=[O:10].O>S(=O)(=O)(O)O>[NH2:1][C:2]1[C:7]([N+:9]([O-:11])=[O:10])=[C:6]([Cl:8])[CH:5]=[CH:4][N:3]=1

Komponenten

5

Edukt 3

HCID 944Nitric AcidHCID 962WaterHCID 5818662-Amino-4-chloropyridine

Produkt 1

HCID 40716944-Chloro-3-nitropyridin-2-amineAusbeute 36 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1118Sulfuric AcidLösungsmittel2×

Versuchsvorschrift

To a solution of 2-amino-4-chloropyridine (5.00 g, 0.0389 mol) in sulfuric acid (40.8 mL) with stirring at 0° C. was added a solution of nitric acid (2.72 g, 0.0389 mol) and sulfuric acid (3.89 g, 0.0389 mol). The mixture was stirred (1 hr) then poured into 200 g ice and 100 ml water. The solid was filtered and collected. The solution was neutralized with 28% NH3 in water to pH ˜5. The solution was extracted with EtOAc (3×300 ml). The solid also was dissolved in EtOAc and neutralized with 28% NH3 in H2O. The organic layers were combined, concentrated with 30 g silica gel, and purified by flash chromatography (20 to 60% EtOAc/hexanes) to afford the title compound (2.40 g, 36%) as a yellow solid.

Aufarbeitung

  1. filtrationThe solid was filtered
  2. customcollected
  3. extractionThe solution was extracted with EtOAc (3×300 ml)
  4. dissolutionThe solid also was dissolved in EtOAc and neutralized with 28% NH3 in H2O
  5. concentrationconcentrated with 30 g silica gel
  6. custompurified by flash chromatography (20 to 60% EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-a1c7f1e645d9486981377f4cf80d6f31
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08481550B2

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