Acetic Acid → N-(2-fluoro-5-nitrophenyl)acetamide

HRID 2266558Notes

Reaction equation

HRID 2266558 reaction equation
C(O[C:5](=[O:7])[CH3:6])(=O)C.[F:8][C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][C:10]=1[NH2:18].C(O)(=O)C>O>[F:8][C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][C:10]=1[NH:18][C:5](=[O:7])[CH3:6]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 7918Acetic AnhydrideHCID 677852-Fluoro-5-nitroaniline

Product 1

HCID 2779405N-(2-fluoro-5-nitrophenyl)acetamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

Acetic anhydride (8.0 mL) was added dropwise over a period of 10 minutes to a mixture of 2-fluoro-5-nitrophenylamine (7.8 g) and acetic acid (50 mL) at reflux. The resulting mixture was heated at reflux for 30 minutes and cooled to 40° C. The mixture was poured into cold water (800 mL) and the resulting precipitate collected by filtration, washed with 1.0 M aqueous hydrochloric acid and water and dried to give title compound as a light brown solid, 9.2 g.

Workup

  1. temperatureat reflux
  2. temperatureThe resulting mixture was heated
  3. temperatureat reflux for 30 minutes
  4. filtrationthe resulting precipitate collected by filtration
  5. washwashed with 1.0 M aqueous hydrochloric acid and water
  6. customdried

Sources & evidence

ORD record
ord-08fed089b01c4df39708421871d8ce18
Source dataset
uspto-grants-2010_12
Patent number
US07858640B2

Reaction notes

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