Nitric Acid → N-[2-Nitro-4-[1-(trifluoroacetyl)-2-pyrrolidinyl]-5-fluorophenyl]trifluoroacetamide

HRID 13399Notes

Reaction equation

HRID 13399 reaction equation
[N+:1]([O-:4])(O)=[O:2].[F:5][C:6]([F:29])([F:28])[C:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([CH:16]2[CH2:20][CH2:19][CH2:18][N:17]2[C:21](=[O:26])[C:22]([F:25])([F:24])[F:23])=[C:12]([F:27])[CH:11]=1)=[O:8]>O>[F:29][C:6]([F:5])([F:28])[C:7]([NH:9][C:10]1[CH:11]=[C:12]([F:27])[C:13]([CH:16]2[CH2:20][CH2:19][CH2:18][N:17]2[C:21](=[O:26])[C:22]([F:23])([F:24])[F:25])=[CH:14][C:15]=1[N+:1]([O-:4])=[O:2])=[O:8]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 23145429HCID 23145429, compound

Product 1

HCID 23145265N-[2-Nitro-4-[1-(trifluoroacetyl)-2-pyrrolidinyl]-5-fluorophenyl]trifluoroacetamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

100 ml of fuming nitric acid was added to 28 g of 2,2,2-trifluoro-N-(3-fluoro-4-(1-(trifluoroacetyl)pyrrolidin-2-yl)phenyl)acetamide with cooling with ice, and the reaction liquid was stirred at room temperature for 1 hour. Water with ice was added to the reaction liquid to dilute it, then extracted with ethyl acetate, washed with saturated saline, and dried with anhydrous magnesium 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=10/1) to obtain the entitled compound as a yellow oily substance.

Workup

  1. temperaturewith cooling with ice
  2. customthe reaction liquid
  3. additionto dilute it
  4. extractionextracted with ethyl acetate
  5. washwashed with saturated saline
  6. dry with materialdried with anhydrous magnesium sulfate
  7. customThe solvent was evaporated away under reduced pressure
  8. customthe resulting residue was purified through silica gel column chromatography (developing solvent: hexane/ethyl acetate=10/1)
  9. customto obtain the entitled compound as a yellow oily substance

Sources & evidence

ORD record
ord-30ca783781e344fda6f5bdc143843efa
Source dataset
uspto-grants-2010_06
Patent number
US07728025B2

Reaction notes

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