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

HRID 1594084Notes

Reaction equation

HRID 1594084 reaction equation
[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

Participants

3

Reactant 2

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

Product 1

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

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-485ed3a14ccd48e08a563536a605c032
Source dataset
uspto-grants-2007_11
Patent number
US07300945B2

Reaction notes

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