Potassium Nitrate → 5-Nitro-2-(trifluoromethyl)quinoline

HRID 2215428Notes

Reaction equation

HRID 2215428 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1.[N+:15]([O-])([O-:17])=[O:16].[K+]>S(=O)(=O)(O)O>[N+:15]([C:9]1[CH:8]=[CH:7][CH:6]=[C:5]2[C:10]=1[CH:11]=[CH:12][C:3]([C:2]([F:1])([F:13])[F:14])=[N:4]2)([O-:17])=[O:16]

Participants

4

Reactant 2

HCID 24434Potassium NitrateHCID 27778052-(Trifluoromethyl)quinoline

Product 1

HCID 219488215-Nitro-2-(trifluoromethyl)quinoline

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

1.52 g (7.7 mmol) of 2-(trifluoromethyl)quinoline is dissolved in 7.90 ml of concentrated sulfuric acid, and 1.47 g of potassium nitrate is added in portions at 0° C. After 20 hours at room temperature, the reaction solution is poured onto ice/water. It is extracted with ethyl acetate, the combined organic phases are washed with saturated sodium bicarbonate solution and dried on sodium sulfate. After removal of the solvent and chromatography on silica gel with hexane-ethyl acetate (10–100%), 390 mg (21% of theory) of the product is obtained.

Workup

  1. additionthe reaction solution is poured onto ice/water
  2. extractionIt is extracted with ethyl acetate
  3. washthe combined organic phases are washed with saturated sodium bicarbonate solution
  4. customdried on sodium sulfate
  5. customAfter removal of the solvent and chromatography on silica gel with hexane-ethyl acetate (10–100%), 390 mg (21% of theory) of the product
  6. customis obtained

Sources & evidence

ORD record
ord-86ff857ea1c243908d118a07329ac912
Source dataset
uspto-grants-2006_09
Patent number
US07109212B2

Reaction notes

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