Potassium Carbonate → 5-Fluoro-2-methyl-4-nitroaniline

HRID 34037Notes

Reaction equation

HRID 34037 reaction equation
[F:1][C:2]1[C:3]([N+:13]([O-:15])=[O:14])=[CH:4][C:5]([CH3:12])=[C:6]([NH:8]C(=O)C)[CH:7]=1.C(=O)([O-])[O-].[K+].[K+]>Cl>[F:1][C:2]1[C:3]([N+:13]([O-:15])=[O:14])=[CH:4][C:5]([CH3:12])=[C:6]([NH2:8])[CH:7]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 23070191N-(5-Fluoro-2-methyl-4-nitrophenyl)acetamide

Product 1

HCID 230701315-Fluoro-2-methyl-4-nitroanilineYield 95.8%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A suspension of 3.5 g of N-(5-fluoro-2-methyl-4-nitrophenyl)-acetamide in 5N hydrochloric acid was heated under reflux for 1 hour. After allowing to cool, the solution was neutralized with potassium carbonate, and extracted with 80 mL of ethylacetate. The organic layer was dried over anhydrous magnesium sulfate, allowed to pass through a silica gel pad, and then the solvent was distilled off under reduced pressure, to afford 2.69 g of the title compound as ocher crystals.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 1 hour
  3. temperatureto cool
  4. extractionextracted with 80 mL of ethylacetate
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-d74a9a52f90b4fe3b7ad88f620945263
Source dataset
uspto-grants-2008_09
Patent number
US07429609B2

Reaction notes

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