Nitric Acid → 3-Chloro-2-(4-chloro-3-nitrophenyl)-5-(trifluoromethyl)pyridine

HRID 1957241Notes

Reaction equation

HRID 1957241 reaction equation
[N+:1]([O-:4])(O)=[O:2].[Cl:5][C:6]1[C:7]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=2)=[N:8][CH:9]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:11]=1>S(=O)(=O)(O)O>[Cl:5][C:6]1[C:7]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[C:18]([N+:1]([O-:4])=[O:2])[CH:17]=2)=[N:8][CH:9]=[C:10]([C:12]([F:14])([F:15])[F:13])[CH:11]=1

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 19068737HCID 19068737, compound

Product 1

HCID 157668793-Chloro-2-(4-chloro-3-nitrophenyl)-5-(trifluoromethyl)pyridine

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

3.6 g (57 mmol) of concentrated nitric acid were added dropwise to a mixture of 11.1 g (38.0 mmol) of 3-chloro-2-(4-chloro-phenyl)-5-trifluoromethylpyridine in 50 ml of concentrated sulfuric acid while stirring and cooling in ice at 0°-5° C. The mixture was stirred at this temperature for two hours and then poured into 500 ml of ice-water. The product was extracted three times with 150 ml of ethyl acetate each time. The combined organic phases were washed twice with a little water, dried over sodium sulfate and finally concentrated under reduced pressure. The residue was purified by chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 95:5). Yield: 11.8 g (90%) of colorless crystals of melting point 68°-69° C.

Workup

  1. temperaturecooling in ice at 0°-5° C
  2. stirringThe mixture was stirred at this temperature for two hours
  3. extractionThe product was extracted three times with 150 ml of ethyl acetate each time
  4. washThe combined organic phases were washed twice with a little water
  5. dry with materialdried over sodium sulfate
  6. concentrationfinally concentrated under reduced pressure
  7. customThe residue was purified by chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 95:5)

Sources & evidence

ORD record
ord-5e12e0cdcf804fceb4bedf0d523afc18
Source dataset
uspto-grants-1998_07
Patent number
US05783522

Reaction notes

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