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

HRID 1594084ノート

反応式

HRID 1594084 の反応式
[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

参加物

3

反応物 2

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

生成物 1

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

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-485ed3a14ccd48e08a563536a605c032
出典データセット
uspto-grants-2007_11
特許番号
US07300945B2

反応ノート

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