Phosphorus oxychloride → (2-Chloro-6-isopropyl-3-nitro-pyridin-4-yl)-ethyl-amine

HRID 895554Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 895554
[CH2:1]([NH:3][C:4]1[CH:9]=[C:8]([CH:10]([CH3:12])[CH3:11])[NH:7][C:6](=O)[C:5]=1[N+:14]([O-:16])=[O:15])[CH3:2].O=P(Cl)(Cl)[Cl:19]>>[Cl:19][C:6]1[C:5]([N+:14]([O-:16])=[O:15])=[C:4]([NH:3][CH2:1][CH3:2])[CH:9]=[C:8]([CH:10]([CH3:12])[CH3:11])[N:7]=1

Komponenten

3

Edukt 2

HCID 24813Phosphorus oxychlorideHCID 223801724-ethylamino-6-isopropyl-3-nitro-1H-pyridin-2-one

Produkt 1

HCID 22379920(2-Chloro-6-isopropyl-3-nitro-pyridin-4-yl)-ethyl-amine

Versuchsvorschrift

A mixture of 4-ethylamino-6-isopropyl-3-nitro-1H-pyridin-2-one (520 mg, 2.31 mmol) in POCl3 is stirred at reflux for 1.5 h. After cooling, the solution is concentrated in vacuo. The reaction flask is then placed in an ice bath and crushed ice is added to the residue. The mixture is swirled vigorously for a few minutes and then stirred at 0° C. for 1 h. The mixture is then extracted with EtOAc. The extract is washed with additional H2O (20 mL) and brine (20 mL). The extract is dried over Na2SO4 and concentrated to afford (2-chloro-6-isopropyl-3-nitro-pyridin-4-yl)-ethyl-amine as a yellow solid. The material is sufficiently pure to be used without further purification. 1H NMR (CDCl3, 400 MHz) δ 6.62 (br, 1H), 6.44 (s, 1H), 3.31 (m, 2H), 2.91 (sept, J=6.8 Hz, 1H), 1.33 (t, J=7.4 Hz, 3H), 1.26 (d, J=6.8 Hz, 6H) ppm.

Aufarbeitung

  1. temperatureat reflux for 1.5 h
  2. temperatureAfter cooling
  3. concentrationthe solution is concentrated in vacuo
  4. customThe reaction flask is then placed in an ice bath
  5. customcrushed ice
  6. additionis added to the residue
  7. waitThe mixture is swirled vigorously for a few minutes
  8. stirringstirred at 0° C. for 1 h
  9. extractionThe mixture is then extracted with EtOAc
  10. washThe extract is washed with additional H2O (20 mL) and brine (20 mL)
  11. dry with materialThe extract is dried over Na2SO4
  12. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-4b3bbb1cdd01404ca848b95cb27d2292
Quelldatensatz
uspto-grants-2005_07
Patentnummer
US06916819B2

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