Nitric Acid → N-[4-fluoro-2-nitro-6-(trifluoromethyl)phenyl]acetamide

HRID 547642Notes

Reaction equation

HRID 547642 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:11])[CH3:10])=[C:4]([C:12]([F:15])([F:14])[F:13])[CH:3]=1.[N+:16]([O-])([OH:18])=[O:17]>OS(O)(=O)=O>[F:1][C:2]1[CH:3]=[C:4]([C:12]([F:13])([F:14])[F:15])[C:5]([NH:8][C:9](=[O:11])[CH3:10])=[C:6]([N+:16]([O-:18])=[O:17])[CH:7]=1

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 10560920N-(4-fluoro-2-(trifluoromethyl)phenyl)acetamide

Product 1

HCID 10778132N-[4-fluoro-2-nitro-6-(trifluoromethyl)phenyl]acetamide

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A solution of 4-fluoro-2-(trifluoromethyl)aniline (5.0 g, 27.91 mmol) in acetic anhydride (25 mL) was stirred at ambient temperature for 3 hours to produce a white needle precipitate. The reaction mixture was poured onto ice water, filtered then dried to give 6.0 g of N-[4-fluoro-2-(trifluoromethyl)phenyl]acetamide as an off-white solid which was used without further purification. The N-[4-fluoro-2-(trifluoromethyl)phenyl]acetamide (2.0 g, 9.04 mmol) was dissolved in concentrated H2SO4 (15 mL) and cooled to 0 degrees Centigrade using an ice bath. 70% HNO3 (1.5 mL) was added drop wise and the reaction stirred at 0 degrees Centigrade for 30 min and then at ambient temperature for 3 hours. The reaction mixture was poured onto ice-water, filtered then dried to give 2.4 g of the desired N-[4-fluoro-2-nitro-6-(trifluoromethyl)phenyl]acetamide.

Workup

  1. customwas used without further purification
  2. temperaturecooled to 0 degrees Centigrade
  3. waitat ambient temperature for 3 hours
  4. additionThe reaction mixture was poured onto ice-water
  5. filtrationfiltered
  6. customthen dried

Sources & evidence

ORD record
ord-1371ed51243f4313b91427b46f460de7
Source dataset
uspto-grants-2011_05
Patent number
US07939528B2

Reaction notes

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