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

HRID 349732Notes

Reaction equation

HRID 349732 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:3]=1[NH2:4].[C:12](OC(=O)C)(=[O:14])[CH3:13].S(=O)(=O)(O)O>>[F:1][C:2]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:3]=1[NH:4][C:12](=[O:14])[CH3:13]

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 7918Acetic AnhydrideHCID 677852-Fluoro-5-nitroaniline

Product 1

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

Conditions

Temperature
100 °C

Procedure

5.0 g (32 mmol) of 2-fluoro-5-nitroaniline were admixed with 10 ml (110 mmol) of acetic anhydride and 0.1 ml of conc. sulfuric acid and stirred at 100° C. for 1.5 hours. The solution was added to 100 ml of ice/water, and the precipitate which formed was filtered off and washed with water. The crude product was purified by chromatography (1:1 ethyl acetate/heptane) on silica gel (yield 5.4 g, 85%).

Workup

  1. customthe precipitate which formed
  2. filtrationwas filtered off
  3. washwashed with water
  4. customThe crude product was purified by chromatography (1:1 ethyl acetate/heptane) on silica gel (yield 5.4 g, 85%)

Sources & evidence

ORD record
ord-6b7a628752e0486c983fa8a366d0a4b0
Source dataset
uspto-grants-2007_02
Patent number
US07179941B2

Reaction notes

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