Quinoline → 2-Chloro-3-nitro-5-(trifluoromethyl)pyridine

HRID 402339Notes

Reaction equation

HRID 402339 reaction equation
O[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([C:11]([F:14])([F:13])[F:12])=[CH:4][N:3]=1.P(Cl)(Cl)([Cl:17])=O.N1C2C(=CC=CC=2)C=CC=1.[OH-].[Na+]>>[Cl:17][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([C:11]([F:14])([F:13])[F:12])=[CH:4][N:3]=1

Participants

5

Reactant 4

HCID 7047QuinolineHCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 178526653HCID 178526653, compound

Product 1

HCID 47369502-Chloro-3-nitro-5-(trifluoromethyl)pyridineYield 85.9%

Procedure

A mixture of 5.22 g of 2-hydroxy-3-nitro-5-(trifluoromethyl)pyridine, 4.2 g of phosphorus oxychloride and 2.0 g of quinoline was refluxed with heating for 5.5 hours. The reaction mixture was cooled down to room temperature, then, the reaction mixture was poured into ice water. This mixture was neutralized with a sodium hydroxide aqueous solution, then, the mixture was extracted with ethyl acetate twice. The combined organic layers were washed with water and saturated saline, dried over magnesium sulfate, then, concentrated under reduced pressure. The residue was subjected to silica gel column chromatography, to obtain 4.88 g of 2-chloro3-nitro-5-(trifluoromethyl)pyridine.

Workup

  1. temperaturewas refluxed
  2. temperaturewith heating for 5.5 hours
  3. extractionthe mixture was extracted with ethyl acetate twice
  4. washThe combined organic layers were washed with water and saturated saline
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4c4ce66dc7b64c73a8b821c0e95fea52
Source dataset
uspto-grants-2014_06
Patent number
US08742112B2

Reaction notes

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