Acetonitrile → 2,3-Dichloro-5-nitropyridine

HRID 898734Notes

Reaction equation

HRID 898734 reaction equation
[Cl:1][C:2]1[C:3](O)=[N:4][CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1.C(#N)C.P(Cl)(Cl)([Cl:17])=O>O>[Cl:17][C:3]1[C:2]([Cl:1])=[CH:7][C:6]([N+:8]([O-:10])=[O:9])=[CH:5][N:4]=1

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 24813Phosphorus oxychlorideHCID 178526838HCID 178526838, compound

Product 1

HCID 27631062,3-Dichloro-5-nitropyridine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
80 °C

Procedure

A mixture of 3-chloro-2-hydroxy-5-nitropyridine (36.0 g), acetonitrile (72 mL), and phosphorus oxychloride (37.5 g) was heated to 80° C. The reaction was then stirred at this temperature for about 15 hours. After cooling the reaction to 40° C., water (27 g) was added, while maintaining the temperature below 70° C. The temperature was adjusted to 45° C., and then more water (189 g) was added slowly. The reaction was then cooled to 23° C., stirred for at least 12 hours, and then filtered. After washing the wet cake with water, the product was dried in a vacuum oven. 1H NMR (400 MHz/CDCl3) δ 9.10 (d, J=2.5 Hz, 1H), 8.56 (d, J=2.4 Hz, 1H)

Workup

  1. temperatureAfter cooling
  2. customthe reaction to 40° C.
  3. temperaturewhile maintaining the temperature below 70° C
  4. customwas adjusted to 45° C.
  5. temperatureThe reaction was then cooled to 23° C.
  6. stirringstirred for at least 12 hours
  7. filtrationfiltered
  8. washAfter washing the wet cake with water
  9. customthe product was dried in a vacuum oven

Sources & evidence

ORD record
ord-5dc4972c408044dfb5694455b9b9175b
Source dataset
uspto-grants-2008_04
Patent number
US07351833B2

Reaction notes

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