Potassium Nitrate → Methyl 5-[4-(ethylsulfonyl)phenoxy]-3-nitro-2-[(2-pyridinylcarbonyl)amino]benzoate

HRID 2080671Notes

Reaction equation

HRID 2080671 reaction equation
[CH2:1]([S:3]([C:6]1[CH:31]=[CH:30][C:9]([O:10][C:11]2[CH:12]=[CH:13][C:14]([NH:21][C:22]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=3)=[O:23])=[C:15]([CH:20]=2)[C:16]([O:18][CH3:19])=[O:17])=[CH:8][CH:7]=1)(=[O:5])=[O:4])[CH3:2].[N+:32]([O-])([O-:34])=[O:33].[K+]>FC(F)(F)C(O)=O>[CH2:1]([S:3]([C:6]1[CH:7]=[CH:8][C:9]([O:10][C:11]2[CH:12]=[C:13]([N+:32]([O-:34])=[O:33])[C:14]([NH:21][C:22]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=3)=[O:23])=[C:15]([CH:20]=2)[C:16]([O:18][CH3:19])=[O:17])=[CH:30][CH:31]=1)(=[O:4])=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 24434Potassium NitrateHCID 67110490Methyl 5-[4-(ethylsulfonyl)phenoxy]-2-[(2-pyridinylcarbonyl)amino]benzoate

Product 1

HCID 57433575Methyl 5-[4-(ethylsulfonyl)phenoxy]-3-nitro-2-[(2-pyridinylcarbonyl)amino]benzoateYield 88.8%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
80 °C

Procedure

1.9 g of methyl 5-[4-(ethylsulfonyl)phenoxy]-2-[(2-pyridinylcarbonyl)amino]benzoate was dissolved in 20 ml of trifluoroacetic acid, and 2.2 g of potassium nitrate was added to it and stirred under heat at 80° C. for 2 hours. The reaction liquid was restored to room temperature, trifluoroacetic acid was evaporated away under reduced pressure, the residue was dissolved in chloroform, and aqueous saturated sodium hydrogencarbonate solution was added to it. This was extracted with chloroform, and the organic layer was washed with saturated saline water. After dried, the solvent was evaporated away under reduced pressure, and the residue was purified through silica gel column chromatography (developing solvent: hexane/ethyl acetate=2/1 to 1/1) to obtain 1.86 g of the entitled compound as a yellow solid.

Workup

  1. customThe reaction liquid
  2. customwas restored to room temperature
  3. customtrifluoroacetic acid was evaporated away under reduced pressure
  4. dissolutionthe residue was dissolved in chloroform
  5. additionaqueous saturated sodium hydrogencarbonate solution was added to it
  6. extractionThis was extracted with chloroform
  7. washthe organic layer was washed with saturated saline water
  8. customAfter dried
  9. customthe solvent was evaporated away under reduced pressure
  10. customthe residue was purified through silica gel column chromatography (developing solvent: hexane/ethyl acetate=2/1 to 1/1)

Sources & evidence

ORD record
ord-5a1badcb29694e3588546adb8b82feb8
Source dataset
uspto-grants-2011_04
Patent number
US07932394B2

Reaction notes

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