Potassium Carbonate → HCID 178498306, compound

HRID 1251915Notes

Reaction equation

HRID 1251915 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([C:14]([O:16][CH3:17])=[O:15])=[CH:12][CH:11]=[CH:10][N+:9]=2[O-])=[CH:4][CH:3]=1.C(=O)([O-])[O-:20].[K+].[K+]>C(OC(=O)C)(=O)C.CO.O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([C:14]([O:16][CH3:17])=[O:15])=[CH:12][CH:11]=[C:10]([OH:20])[N:9]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 11430Potassium CarbonateHCID 183245012-(4-Fluorophenyl)-3-(methoxycarbonyl)pyridine-1-oxide

Product 1

HCID 178498306HCID 178498306, compoundYield 76.2%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 7918Acetic AnhydrideSolvent

Procedure

A solution of 2-(4-fluorophenyl)-3-(methoxycarbonyl)pyridine-1-oxide (10.5 g.) in acetic anhydride (500 ml.) was stirred at reflux for 17 hr., cooled, evaporated to dryness and the residue partitioned between saturated sodium bicarbonate solution and ethyl acetate. The organic layer was separated, dried and evaporated to dryness. The gum obtained was dissolved in methanol (400 ml.), treated with a solution of potassium carbonate (11.7 g.) in water (100 ml) and stirred at ambient temperature for 2 hours. The methanol was evaporated off, the aqueous residue diluted with more water (200 ml.) and the mixture filtered to give methyl 2-(4-fluorophenyl)-6-hydroxypyridin-3-carboxylate (8.0 g.) as a brown solid.

Workup

  1. temperatureat reflux for 17 hr
  2. temperature, cooled
  3. customevaporated to dryness
  4. customthe residue partitioned between saturated sodium bicarbonate solution and ethyl acetate
  5. customThe organic layer was separated
  6. customdried
  7. customevaporated to dryness
  8. customThe gum obtained
  9. customThe methanol was evaporated off
  10. additionthe aqueous residue diluted with more water (200 ml.)
  11. filtrationthe mixture filtered

Sources & evidence

ORD record
ord-c10c598bafa443a9814c801f8a285ca6
Source dataset
uspto-grants-2002_01
Patent number
US06342765B1

Reaction notes

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