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

HRID 1988739노트

반응식

HRID 1988739 반응식
[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

참가 물질

3

반응물 2

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

생성물 1

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

실험 절차

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 (CDCl2, 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.

후처리

  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

출처 및 근거

ORD 기록
ord-b67d216b478847dc8324e143a341e09a
출처 데이터셋
uspto-grants-2010_01
특허 번호
US07642267B2

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