Nitric Acid → N-(4-ethyl-3-nitro-phenyl)-acetamide

HRID 1773541Notes

Reaction equation

HRID 1773541 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:12])[CH3:11])=[CH:5][CH:4]=1)[CH3:2].[N+:13]([O-])([OH:15])=[O:14].C(=O)([O-])[O-].[Na+].[Na+]>>[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:12])[CH3:11])=[CH:5][C:4]=1[N+:13]([O-:15])=[O:14])[CH3:2]

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 10340Sodium CarbonateHCID 72893N-(4-Ethylphenyl)acetamide

Product 1

HCID 22708659N-(4-ethyl-3-nitro-phenyl)-acetamideYield 88%

Conditions

Temperature
-15 °C

Procedure

To concentrate sulfuric acid (8 mL) was added portionwise N-(4-ethyl-phenyl)-acetamide (2.0 g, 12.27 mmol) and the mixture was cooled to −15° C., fuming nitric acid (0.505 mL, 12.27 mmol) was then added dropwise. The reaction mixture was stirred at a temperature ranging between −20 and −10° C. for 75 minutes. The reaction mixture was then poured into ice, neutralized by addition of sodium carbonate and extracted twice with diethyl ether. The combined organic extracts were dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure. The crude residue was purified by flash chromatography (hexane/EtOAc, 100/0 to 70/30) to give 2.231 g (88% yield) of N-(4-ethyl-3-nitro-phenyl)-acetamide.

Workup

  1. concentrationTo concentrate sulfuric acid (8 mL)
  2. additionThe reaction mixture was then poured into ice
  3. extractionextracted twice with diethyl ether
  4. dry with materialThe combined organic extracts were dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customThe crude residue was purified by flash chromatography (hexane/EtOAc, 100/0 to 70/30)

Sources & evidence

ORD record
ord-4e84c3807abc4f8383d13013d6c882fb
Source dataset
uspto-grants-2016_02
Patent number
US09255110B2

Reaction notes

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