Phosphorus oxychloride → 2-Chloro-4-methyl-5-nitropyridine

HRID 1993631Notes

Reaction equation

HRID 1993631 reaction equation
P(Cl)(Cl)(Cl)=O.P(Cl)(Cl)(Cl)(Cl)[Cl:7].[CH3:12][C:13]1[C:18]([N+:19]([O-:21])=[O:20])=[CH:17][N:16]=[C:15](O)[CH:14]=1>>[Cl:7][C:15]1[CH:14]=[C:13]([CH3:12])[C:18]([N+:19]([O-:21])=[O:20])=[CH:17][N:16]=1

Participants

4

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 24819Phosphorus pentachlorideHCID 178429283HCID 178429283, compound

Product 1

HCID 3453642-Chloro-4-methyl-5-nitropyridine

Conditions

Temperature
120 °C

Procedure

Add phosphorus oxychloride (0.6 mmol, 0.05 mL) and phosphorus pentachloride (0.6 mmol, 0.12 g) over 4-methyl-5-nitro-pyridin-2-ol (1.9 mmol, 0.3 g). Stir at 120° C. for 1.5 hours. Cool down, add ice-water and extract in CH2Cl2. Wash combined organic layers with saturated aq. sodium chloride solution. Dry over sodium sulfate, filter, and concentrate under reduced pressure to give 2-chloro-4-methyl-5-nitro-pyridine.

Workup

  1. temperatureCool down
  2. extractionextract in CH2Cl2
  3. washWash
  4. dry with materialDry over sodium sulfate
  5. filtrationfilter
  6. concentrationconcentrate under reduced pressure

Sources & evidence

ORD record
ord-22d6ad8e5fcd4c4395075f884ce7e6cd
Source dataset
uspto-grants-2010_01
Patent number
US07652015B2

Reaction notes

Loading…