Sulfuric Acid → 2,6-Dichloro-5-fluoronicotinamide

HRID 1599019Notes

Reaction equation

HRID 1599019 reaction equation
S(=O)(=O)(O)[OH:2].[Cl:6][C:7]1[C:12]([C:13]#[N:14])=[CH:11][C:10]([F:15])=[C:9]([Cl:16])[N:8]=1>>[Cl:6][C:7]1[N:8]=[C:9]([Cl:16])[C:10]([F:15])=[CH:11][C:12]=1[C:13]([NH2:14])=[O:2]

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 27338492,6-Dichloro-5-fluoro-3-pyridinecarbonitrile

Product 1

HCID 27740222,6-Dichloro-5-fluoronicotinamide

Conditions

Temperature
75 °C

Procedure

The amide was prepared by addition of concentrated sulfuric acid, 185 kg, to the 2,6-dichloro-3-cyano-5-fluoropyridine (2) residue prepared in Example 2b. The mixture was heated at about 75° C. for 1 hour. The solution was cooled and added to 360 kg of ice water. The suspension formed was extracted with isopropyl alcohol/chloroform (30:70). The organic layer was removed and dried. The solvent was evaporated to provide the title compound.

Workup

  1. temperatureThe solution was cooled
  2. customThe suspension formed
  3. extractionwas extracted with isopropyl alcohol/chloroform (30:70)
  4. customThe organic layer was removed
  5. customdried
  6. customThe solvent was evaporated

Sources & evidence

ORD record
ord-0628f32849034c4d918de7dc620cf452
Source dataset
uspto-grants-1998_04
Patent number
US05739342

Reaction notes

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