Sodium Hydroxide → 2,6-Dichloro-3-nitropyridin-4-amine

HRID 81203

Reaktionsgleichung

Reaktionsgleichung von HRID 81203
[Cl:1][C:2]1[CH:7]=[C:6]([NH:8][N+]([O-])=O)[CH:5]=[C:4]([Cl:12])[N:3]=1.[OH-:13].[Na+].[NH4+:15].[OH-:16]>OS(O)(=O)=O>[Cl:12][C:4]1[C:5]([N+:15]([O-:16])=[O:13])=[C:6]([NH2:8])[CH:7]=[C:2]([Cl:1])[N:3]=1

Komponenten

5

Edukt 3

HCID 14798Sodium HydroxideHCID 14923Ammonium HydroxideHCID 4216172,6-Dichloro-4-nitraminopyridine

Produkt 1

HCID 2827402,6-Dichloro-3-nitropyridin-4-amine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1118Sulfuric AcidLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

N-(2,6-dichloropyridin-4-yl)nitramide (205 g crude, 0.617 mol) was added carefully to conc. H2SO4 (800 mL) at room temperature. Then the reaction mixture was stirred at 80° C. for 2 h. TLC (Petroleum ether/ethyl acetate=2:1) showed the reaction was complete. The mixture was cooled to room temperature and poured into crushed ice. The mixture was cooled to 0° C. and neutralized with NaOH and NH4OH. The resulting precipitate was collected by filtration and washed with water. The resulting precipitate was dissolved in ethyl acetate, dried over Na2SO4 and concentrated to give crude 2,6-dichloro-3-nitropyridin-4-amine, which was used for the next step without further purification. 1H NMR (400 MHz, CDCl3) δ: 7.64 (s, 2H), 6.86 (s, 1H).

Aufarbeitung

  1. temperatureThe mixture was cooled to room temperature
  2. additionpoured
  3. custominto crushed ice
  4. filtrationThe resulting precipitate was collected by filtration
  5. washwashed with water
  6. dissolutionThe resulting precipitate was dissolved in ethyl acetate
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-9d7db0f3aef242cc9de2a17fc10cb115
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846657B2

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