Phosphorus oxychloride → 6-Chloro-2-methyl-3-nitropyridine

HRID 1075561Notes

Reaction equation

HRID 1075561 reaction equation
O[C:2]1[N:7]=[C:6]([CH3:8])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][CH:3]=1.P(Cl)(Cl)(Cl)(Cl)[Cl:13].P(Cl)(Cl)(Cl)=O>>[Cl:13][C:2]1[N:7]=[C:6]([CH3:8])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 24813Phosphorus oxychloride2×HCID 24819Phosphorus pentachloride2×HCID 178433443HCID 178433443, compound

Product 1

HCID 2531236-Chloro-2-methyl-3-nitropyridineYield 277.5%

Conditions

Temperature
110 °C

Procedure

A mixture of 2.42 gm (15.7 mMol) 6-hydroxy-3-nitro-2-picoline, 1.0 gm phosphorus pentachloride, and 0.5 mL phosphorus oxychloride was heated at 110° C. for 2.5 hours. The reaction mixture was cooled to room temperature and then an additional 0.5 gm of phosphorus pentachloride and 0.5 mL phosphorus oxychloride were added. Heating was resumed for one hour at which point the reaction mixture poured into 100 mL of an ice/water slurry. The resultant slurry is filtered and the solid dried under vacuum to provide 2.3 gm (85%) of the desired compound as a brown solid.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. temperatureHeating
  3. filtrationThe resultant slurry is filtered
  4. customthe solid dried under vacuum

Sources & evidence

ORD record
ord-18c4a63d41184e8ba80dc29d6d5571ea
Source dataset
uspto-grants-1999_05
Patent number
US05905084

Reaction notes

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