Potassium Nitrate → 5-Fluoro-4-(6-ethanesulfonyl-pyridin-3-yloxy)-2-nitro-phenylamine

HRID 13307Notes

Reaction equation

HRID 13307 reaction equation
[N+:1]([O-:4])([O-])=[O:2].[K+].[F:6][C:7]1[CH:8]=[C:9]([NH2:25])[CH:10]=[CH:11][C:12]=1[O:13][C:14]1[CH:15]=[N:16][C:17]([S:20]([CH2:23][CH3:24])(=[O:22])=[O:21])=[CH:18][CH:19]=1>FC(F)(F)C(O)=O>[F:6][C:7]1[C:12]([O:13][C:14]2[CH:15]=[N:16][C:17]([S:20]([CH2:23][CH3:24])(=[O:22])=[O:21])=[CH:18][CH:19]=2)=[CH:11][C:10]([N+:1]([O-:4])=[O:2])=[C:9]([NH2:25])[CH:8]=1

Participants

4

Reactant 2

HCID 24434Potassium NitrateHCID 231456053-Fluoro-4-(6-ethanesulfonyl-pyridin-3-yloxy)-phenylamine

Product 1

HCID 231450955-Fluoro-4-(6-ethanesulfonyl-pyridin-3-yloxy)-2-nitro-phenylamine

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

3.8 g of potassium nitrate was added to a trifluoroacetic acid (100 ml) solution of 10.5 g of 3-fluoro-4-(6-ethanesulfonyl-pyridin-3-yloxy)-phenylamine, and the reaction liquid was stirred for 1 hour at room temperature, and 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 sodium sulfate. The solvent was evaporated away under reduced pressure, and the resulting residue was purified through silica gel column chromatography (developing solvent: hexane/ethyl acetate=1/2) to obtain the entitled compound.

Workup

  1. customthe reaction liquid
  2. customthe solvent was evaporated away under reduced pressure
  3. additionThe residue was diluted with ethyl acetate
  4. washwashed with aqueous saturated sodium bicarbonate and saturated saline in order
  5. dry with materialdried with anhydrous sodium sulfate
  6. customThe solvent was evaporated away under reduced pressure
  7. customthe resulting residue was purified through silica gel column chromatography (developing solvent: hexane/ethyl acetate=1/2)
  8. customto obtain the entitled compound

Sources & evidence

ORD record
ord-37e3c2824ee24e1991bba8bd626a02a6
Source dataset
uspto-grants-2010_06
Patent number
US07728025B2

Reaction notes

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