Ammonia → 2,5-Dichloro-3,6-difluoropyridin-4-amine

HRID 1274724Notes

Reaction equation

HRID 1274724 reaction equation
C(Cl)(Cl)Cl.[Cl:5][C:6]1[C:11]([F:12])=[C:10]([N:13]2C(=O)C3=CC=CC=C3C2=O)[C:9]([Cl:24])=[C:8]([F:25])[N:7]=1.N>CO>[NH2:13][C:10]1[C:9]([Cl:24])=[C:8]([F:25])[N:7]=[C:6]([Cl:5])[C:11]=1[F:12]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 6212ChloroformHCID 22121238N-(2,5-dichloro-3,6-difluoropyridin-4-yl)phthalimide

Product 1

HCID 221211852,5-Dichloro-3,6-difluoropyridin-4-amineYield 46.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixed solution of 100 ml chloroform and 40 ml methanol was added 16.2 g of N-(2,5-dichloro-3,6-difluoropyridine-4-yl)phthalimide together with 20 ml of 25% aqueous solution of ammonia, and the mixture was stirred at room temperature for 30 minutes. The solution was concentrated under reduced pressure, and after adding 150 ml of chloroform to the residue, the mixture was washed with 20 ml of 15% aqueous solution of ammonia, and then, with 10 ml of distilled water. The chloroform layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to obtain 4.55 g of the title compound as a colorless powder.

Workup

  1. concentrationThe solution was concentrated under reduced pressure
  2. additionafter adding 150 ml of chloroform to the residue
  3. washthe mixture was washed with 20 ml of 15% aqueous solution of ammonia
  4. dry with materialThe chloroform layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-53dd904bdfeb4fafa8f268d54926eb35
Source dataset
uspto-grants-2000_12
Patent number
US06156903

Reaction notes

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