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

HRID 34036Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 34036
[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

Komponenten

4

Edukt 2

HCID 944Nitric AcidHCID 35231182-Acetamido-4-fluorotoluene

Produkt 1

HCID 23070191N-(5-Fluoro-2-methyl-4-nitrophenyl)acetamideAusbeute 57,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1118Sulfuric AcidLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-03e403ee7a0841b1832675afc4bff51d
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07429609B2

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