Nitric Acid → 5-Acetamido-2-nitrophenyl acetate

HRID 1773554Notes

Reaction equation

HRID 1773554 reaction equation
[C:1]([NH:4][C:5]1[CH:6]=[C:7]([O:11][C:12](=[O:14])[CH3:13])[CH:8]=[CH:9][CH:10]=1)(=[O:3])[CH3:2].[N+:15]([O-])([OH:17])=[O:16]>>[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([N+:15]([O-:17])=[O:16])=[C:7]([O:11][C:12](=[O:14])[CH3:13])[CH:6]=1)(=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 944Nitric AcidHCID 231988(3-Acetamidophenyl) acetate

Product 1

HCID 127921275-Acetamido-2-nitrophenyl acetateYield 77%

Conditions

Temperature
-10 °C

Procedure

Acetic acid 3-acetylamino-phenyl ester (21.7 g, 112.4 mmol) was added portionwise, at −15° C., to fuming nitric acid (109 mL) maintaining the temperature below −10° C. The reaction mixture was stirred at −10° C. for 3 hours and then was poured into ice. The resulting mixture was extracted 3 times with ethyl acetate and the combined organic extracts were washed with brine, dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure. The crude residue was purified by flash chromatography (EtOAc/hexane, 1/1) to afford 20.608 g (77% yield) of acetic acid 5-acetylamino-2-nitro-phenyl ester as a cream colored solid.

Workup

  1. temperaturemaintaining the temperature below −10° C
  2. additionwas poured into ice
  3. extractionThe resulting mixture was extracted 3 times with ethyl acetate
  4. washthe combined organic extracts were washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customevaporated under reduced pressure
  8. customThe crude residue was purified by flash chromatography (EtOAc/hexane, 1/1)

Sources & evidence

ORD record
ord-2034a231e6fc4e81b6f8ba41fb0cef96
Source dataset
uspto-grants-2016_02
Patent number
US09255110B2

Reaction notes

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