Hydrochloric Acid → 5-Fluoro-4-methylpyridin-2-amine

HRID 1828543Notes

Reaction equation

HRID 1828543 reaction equation
[F:1][C:2]1[C:3]([CH3:12])=[CH:4][C:5]([NH:8]C(=O)C)=[N:6][CH:7]=1.Cl>C(O)C>[F:1][C:2]1[C:3]([CH3:12])=[CH:4][C:5]([NH2:8])=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 2763162N-(5-fluoro-4-methylpyridin-2-yl)acetamide2×

Product 1

HCID 220636705-Fluoro-4-methylpyridin-2-amineYield 88.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The N1-(5-fluoro-4-methyl-2-pyridyl)acetamide (4.25 g, 25.3 mmol) obtained in (D) was dissolved in ethanol (3ml), added with 6 M aqueous hydrochloric acid (3ml) and refluxed by heating for 1 hour and 30 minutes. The reaction mixture was left stand for cooling and the solvent was concentrated. The resulting residue was dissolved in distilled water, and the system was made basic with 1 N aqueous sodium hydroxide and extracted twice with chloroform. The organic layer was dried over anhydrous magnesium sulfate and the solvent was evaporated to obtain the title compound (2.82 g, 88%) as solid.

Workup

  1. temperaturerefluxed
  2. temperatureby heating for 1 hour and 30 minutes
  3. waitThe reaction mixture was left stand
  4. temperaturefor cooling
  5. concentrationthe solvent was concentrated
  6. dissolutionThe resulting residue was dissolved in distilled water
  7. extractionextracted twice with chloroform
  8. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  9. customthe solvent was evaporated

Sources & evidence

ORD record
ord-c862f786502646c3836b4dfaa4c56ff7
Source dataset
uspto-grants-2006_06
Patent number
US07056917B2

Reaction notes

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