Reaction #41534

Reaction equation

potassium nitrate

3-chloro-2,4-bis(pyridin-3-yloxy)aniline

→

compound

3-chloro-2,4-bis(pyridin-3-yloxy)-6-nitroaniline

Solvents

trifluoroacetic acid

Conditions

Workup

1. 1
   Otherthe reaction liquid
2. 2
   Otherthe solvent was evaporated away under reduced pressure
3. 3
   workup.ADDITIONThe residue was diluted with ethyl acetate
4. 4
   Washwashed with aqueous saturated sodium bicarbonate and saturated saline in order
5. 5
   Dryingdried with anhydrous magnesium sulfate
6. 6
   OtherThe solvent was evaporated away under reduced pressure
7. 7
   Otherthe resulting residue was purified with silica gel column chromatography (developing solvent: hexane/ethyl acetate=1/1 to ethyl acetate)

Procedure

315 mg of potassium nitrate was added to a trifluoroacetic acid (20 ml) solution of 891 mg of 3-chloro-2,4-bis(pyridin-3-yloxy)aniline, and the reaction liquid was stirred overnight at room temperature, and then the solvent was evaporated away under reduced pressure. The residue was diluted with ethyl acetate, washed with aqueous saturated sodium bicarbonate and saturated saline in order, and dried with anhydrous magnesium sulfate. The solvent was evaporated away under reduced pressure, and the resulting residue was purified with silica gel column chromatography (developing solvent: hexane/ethyl acetate=1/1 to ethyl acetate) to obtain the entitled compound as an orange solid.

Source