Ethyl 2,6-dichloro-5-fluoropyridine-3-carboxylate → 2,6-Dichloro-5-fluoronicotinic acid

HRID 47878Notes

Reaction equation

HRID 47878 reaction equation
[Cl:1][C:2]1[N:12]=[C:11]([Cl:13])[C:10]([F:14])=[CH:9][C:3]=1[C:4]([O:6]CC)=[O:5]>FC(F)(F)C(O)=O.Cl>[Cl:1][C:2]1[N:12]=[C:11]([Cl:13])[C:10]([F:14])=[CH:9][C:3]=1[C:4]([OH:6])=[O:5]

Participants

4

Reactant 1

HCID 13210747Ethyl 2,6-dichloro-5-fluoropyridine-3-carboxylate

Product 1

HCID 27336592,6-Dichloro-5-fluoronicotinic acidYield 62.3%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

Ethyl 2,6-dichloro-5-fluoronicotinate (1) (30.0 g) was dissolved in a mixture of 60 mL of trifluoro acetic acid and 60 mL of 7.5 N HCl. The mixture was refluxed with stirring for 26 h. It was cooled and the trifluoroacetic acid was removed under reduced pressure. The solution was mixed with 150 mL water, the resulting precipitate was filtered, washed with hexane and dried to yield 16.5 g of 2,6-dichloro-5-fluoro nicotinic acid (2). m.p.=152-156° C.

Workup

  1. temperatureThe mixture was refluxed
  2. temperatureIt was cooled
  3. customthe trifluoroacetic acid was removed under reduced pressure
  4. additionThe solution was mixed with 150 mL water
  5. filtrationthe resulting precipitate was filtered
  6. washwashed with hexane
  7. customdried

Sources & evidence

ORD record
ord-a5737dce6e764e158f8936e8ce98673c
Source dataset
uspto-grants-2004_03
Patent number
US06699989B1

Reaction notes

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