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

HRID 363322Notes

Reaction equation

HRID 363322 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-5be2ebc1bf674676ad62f742cb366955
Source dataset
uspto-grants-1999_02
Patent number
US05874427

Reaction notes

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