Nitric Acid → N-(5-Fluoro-2-methyl-4-nitrophenyl)acetamide

HRID 34036Notes

Reaction equation

HRID 34036 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:12])=[C:6]([NH:8][C:9](=[O:11])[CH3:10])[CH:7]=1.[N+:13]([O-])([OH:15])=[O:14]>S(=O)(=O)(O)O>[F:1][C:2]1[C:3]([N+:13]([O-:15])=[O:14])=[CH:4][C:5]([CH3:12])=[C:6]([NH:8][C:9](=[O:11])[CH3:10])[CH:7]=1

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 35231182-Acetamido-4-fluorotoluene

Product 1

HCID 23070191N-(5-Fluoro-2-methyl-4-nitrophenyl)acetamideYield 57.9%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To a solution of 5.01 g of N-(5-fluoro-2-methyl-phenyl)-acetamide in 30 mL of concentrated sulfuric acid was added dropwise 2.74 g of 70% nitric acid (d=1.42) while keeping the inner temperature at 3° C. After stirring for 40 minutes at this temperature, the reaction solution was poured dropwise into ice water under stirring. After collecting the precipitated powder by filtration, the powder was dissolved in 100 mL of ethyl acetate, washed successively with saturated aqueous sodium hydrogen carbonate (twice) and saturated brine. After drying over anhydrous magnesium sulfate, the solvent was evaporated. The residue was crystallized from ethanol, to afford 3.68 g of the title compound as yellow needle crystals.

Workup

  1. customat 3° C
  2. stirringunder stirring
  3. customAfter collecting the precipitated powder
  4. filtrationby filtration
  5. dissolutionthe powder was dissolved in 100 mL of ethyl acetate
  6. washwashed successively with saturated aqueous sodium hydrogen carbonate (twice) and saturated brine
  7. dry with materialAfter drying over anhydrous magnesium sulfate
  8. customthe solvent was evaporated
  9. customThe residue was crystallized from ethanol

Sources & evidence

ORD record
ord-03e403ee7a0841b1832675afc4bff51d
Source dataset
uspto-grants-2008_09
Patent number
US07429609B2

Reaction notes

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