Nitric Acid → N-(4-fluoro-2-methyl-6-nitrophenyl)acetamide

HRID 2203207

Reaktionsgleichung

Reaktionsgleichung von HRID 2203207
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:11])[CH3:10])=[C:4]([CH3:12])[CH:3]=1.[N+:13]([O-])([OH:15])=[O:14]>O(C(C)=O)C(C)=O>[F:1][C:2]1[CH:7]=[C:6]([N+:13]([O-:15])=[O:14])[C:5]([NH:8][C:9](=[O:11])[CH3:10])=[C:4]([CH3:12])[CH:3]=1

Komponenten

4

Edukt 2

HCID 944Nitric AcidHCID 2737623N-(4-Fluoro-2-methylphenyl)acetamide

Produkt 1

HCID 54330341N-(4-fluoro-2-methyl-6-nitrophenyl)acetamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7918Acetic AnhydrideLösungsmittel

Versuchsvorschrift

To a mixture of N-(4-fluoro-2-methylphenyl)acetamide (19 g, 113.1 mmol, 1 eq) and (CH3CO)2O (190 mL) was added HNO3 (11.4 mL, 1.0 eq) dropwise at 0° C. The reaction mixture was allowed to warm to RT overnight and was subsequently poured onto ice and extracted with DCM. The organic phase was washed with aqueous NaHCO3 until the pH of the aqueous layer was >7. The organic phase was washed with water and then dried over Na2SO4. The solvent was evaporated to give the title compound as a crude solid (20 g, 84%). 1H NMR (400 MHz, DMSO-d6) δ ppm 9.82 (1H, s), 7.71 (1H, dd, J1=2.8 Hz, J2=8.0 Hz), 7.56 (1H, dd, J1=2.8 Hz, J2=9.2 Hz), 2.32 (3H, s), 2.02 (3H, s).

Aufarbeitung

  1. additionwas subsequently poured onto ice
  2. extractionextracted with DCM
  3. washThe organic phase was washed with aqueous NaHCO3 until the pH of the aqueous layer
  4. washThe organic phase was washed with water
  5. dry with materialdried over Na2SO4
  6. customThe solvent was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-2698caa59a6e4839b7403b82b48cf81c
Quelldatensatz
uspto-grants-2016_06
Patentnummer
US09365566B2

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