Nitric Acid → N-(4-ethyl-2-nitrophenyl)acetamide

HRID 2105007Notes

Reaction equation

HRID 2105007 reaction equation
C(O[C:5](=[O:7])[CH3:6])(=O)C.[CH2:8]([C:10]1[CH:16]=[CH:15][C:13]([NH2:14])=[CH:12][CH:11]=1)[CH3:9].[N+:17]([O-])([OH:19])=[O:18]>CCOC(C)=O>[CH2:8]([C:10]1[CH:16]=[CH:15][C:13]([NH:14][C:5](=[O:7])[CH3:6])=[C:12]([N+:17]([O-:19])=[O:18])[CH:11]=1)[CH3:9]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 7918Acetic AnhydrideHCID 115044-Ethylaniline

Product 1

HCID 15919553N-(4-ethyl-2-nitrophenyl)acetamide

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To 5 mL acetic anhydride, was added 4-ethylaniline (0.50 mL, 4.02 mmol). The mixture was cooled to 0° C., then fuming red nitric acid (0.35 mL) was added, dropwise. The mixture was stirred at rt for 15 h, then was diluted with EtOAc. The organic phase was washed with sat. NaHCO3, water and brine, dried (Na2SO4) and concentrated to afford 555 mg of Intermediate 180.1, which was used in the following step without further purification.

Workup

  1. additionwas added
  2. washThe organic phase was washed with sat. NaHCO3, water and brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-5aa1888fe0814888b0c57f554f403ad7
Source dataset
uspto-grants-2009_08
Patent number
US07576098B2

Reaction notes

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