Diethylamine → N-Ethyl-4-nitro-1-oxo-1lambda~5~-pyridin-3-amine

HRID 895542Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 895542
C([O-])([O-])=O.[K+].[K+].Cl[C:8]1[CH:9]=[N+:10]([O-:17])[CH:11]=[CH:12][C:13]=1[N+:14]([O-:16])=[O:15].[CH2:18]([NH:20]CC)[CH3:19]>C1COCC1>[CH2:18]([NH:20][C:8]1[CH:9]=[N+:10]([O-:17])[CH:11]=[CH:12][C:13]=1[N+:14]([O-:16])=[O:15])[CH3:19]

Komponenten

5

Edukt 3

HCID 8021Diethylamine2×HCID 11430Potassium CarbonateHCID 5998173-Chloro-4-nitropyridine N-oxide

Produkt 1

HCID 12343672N-Ethyl-4-nitro-1-oxo-1lambda~5~-pyridin-3-amine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Anhydrous K2CO3 (19 g, 144.5 mmol) is suspended in a solution of 3-Chloro-4-nitro-pyridine-1-oxide (10 g, 57.8 mmol) in anhydrous acetonitrle (100 mL). Excess diethyl amine (2.0 M) in THF is added to the above suspension under cold conditions (ice-bath). After complete addition of diethyl amine, the reaction mixture is allowed to warm to room temperature and left stirring overnight. The reaction mixture is filtered to remove K2CO3 and the filtrate evaporated under reduced pressure to remove volatile solvents. The organic residue is subjected to chromatography, eluting with 30% EtOAc-hexanes to afford 3-Ethylamino-4-nitro-pyridine-1-oxide as an orange solid. 1H NMR (300 MHz, CDCl3) δ 8.0 1 (d, J=7.5 Hz, 1H), 7.91(s, 1H), 7.8 (brs, NH), 7.44 (d, J=7.2 Hz, 1H), 3.30 (t, J=7.2 Hz, 2H), 1.39 (t, J=7.2 Hz, 3H), m/z 184 [M+1]

Aufarbeitung

  1. waitleft
  2. filtrationThe reaction mixture is filtered
  3. customto remove K2CO3
  4. customthe filtrate evaporated under reduced pressure
  5. customto remove volatile solvents
  6. washeluting with 30% EtOAc-hexanes

Quellen und Nachweise

ORD-Eintrag
ord-89545eb069b44dc197c2bec025cd03c5
Quelldatensatz
uspto-grants-2005_07
Patentnummer
US06916819B2

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