Sodium Hydroxide → HCID 21391407, compound

HRID 461580Notes

Reaction equation

HRID 461580 reaction equation
[Cl:1][C:2]1[C:3](F)=[N:4][C:5]([F:10])=[C:6]([Cl:9])[C:7]=1[Cl:8].[OH-:12].[Na+]>O1CCOCC1.O>[Cl:1][C:2]1[C:3](=[O:12])[NH:4][C:5]([F:10])=[C:6]([Cl:9])[C:7]=1[Cl:8]

Participants

5

Reactant 2

HCID 14798Sodium Hydroxide3×HCID 6453828Pyridine, 3,4,5-trichloro-2,6-difluoro-

Product 1

HCID 21391407HCID 21391407, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent3×HCID 312751,4-DioxaneSolvent

Procedure

A solution of 3,4,5-trichlorodifluoropyridine (21.8 g.) in dioxan (220 ml.) was refluxed with a solution of sodium hydroxide (8 g.) in water (40 ml.). After 2 hours a further 8 g. of sodium hydroxide in water (40 ml.) was added (4 molar equivalents of sodium hydroxide in toto). After a further 2 hours, water was added to produce a homogeneous solution which was acidified to precipitate the product (17.6 g., m.p. 170°-4°). After initial purification by charcoal and silica gel column, crystallisation from benzene gave 3,4,5-trichloro-6-fluoro-2-pyridone, m.p. 172°-6°(11.8 g.), having a pale yellow colour. After vacuum sublimation at 100°-120°, the white microcrystals melted at 173°-4° (10.65 g/.).

Workup

  1. waitAfter a further 2 hours
  2. customto produce a homogeneous solution which
  3. customto precipitate the product (17.6 g., m.p. 170°-4°)
  4. customAfter initial purification
  5. customby charcoal and silica gel column, crystallisation from benzene

Sources & evidence

ORD record
ord-a913e5eee14e4872bfb493cbb5d08548
Source dataset
uspto-grants-1977_12
Patent number
US04063926

Reaction notes

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