Sodium Hydroxide → HCID 61728956, compound

HRID 1921282Notes

Reaction equation

HRID 1921282 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[N:9]1[C:14](=[O:15])[CH:13]=[CH:12][C:11]([C:16]([O:18]C)=[O:17])=[CH:10]1.[OH-].[Na+]>CCO.C1COCC1>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[N:9]1[C:14](=[O:15])[CH:13]=[CH:12][C:11]([C:16]([OH:18])=[O:17])=[CH:10]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 67056864HCID 67056864, compound

Product 1

HCID 61728956HCID 61728956, compoundYield 92.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 1-(2,6-difluorophenyl)-6-oxo-1,6-dihydro-3-pyridinecarboxylate (5.41 g) in a mixture of EtOH (108 mL) and THF (54 mL) was added 1 M aqueous NaOH (82 mL) at 0° C., and the mixture was stirred at the same temperature for 2 hr. The mixture was concentrated under reduced pressure and the residue was treated with 1 M HCl (160 mL). The precipitates produced were collected by filtration and dried under reduced pressure at 60° C. to give 1-(2,6-difluorophenyl)-6-oxo-1,6-dihydro-3-pyridinecarboxylic acid (4.73 g).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. additionthe residue was treated with 1 M HCl (160 mL)
  3. customThe precipitates produced
  4. filtrationwere collected by filtration
  5. customdried under reduced pressure at 60° C.

Sources & evidence

ORD record
ord-b250d2de67814432a3c6b8a437093f1d
Source dataset
uspto-grants-2012_05
Patent number
US08173684B2

Reaction notes

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