Sodium Hydroxide → HCID 178524137, compound

HRID 1790331Notes

Reaction equation

HRID 1790331 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([C:13]3[CH:18]=[CH:17][N:16]=[C:15]([C:19]([O-:21])=[O:20])[CH:14]=3)=[CH:11][NH:10][N:9]=2)=[CH:4][CH:3]=1.[OH-].[Na+]>C(O)C.O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([C:13]3[CH:18]=[CH:17][N:16]=[C:15]([C:19]([OH:21])=[O:20])[CH:14]=3)=[CH:11][NH:10][N:9]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 178524136HCID 178524136, compound

Product 1

HCID 178524137HCID 178524137, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 4-[3-(4-fluorophenyl)-1H-pyrazol-4-yl]-2-pyridinecarboxylate prepared as set forth in Example A-224 (0.90 g, 0.003 mol) in 10 mL of ethanol was added a solution of sodium hydroxide (0.24 g, 0.006 mol) in 5 mL of water. The reaction mixture was heated at reflux for 10 hours. After the removal of solvent, the residue was dissolved in water and acidified with citric acid solution to pH 5. Then the aqueous phase was extracted with ethyl acetate and the organic phase was dried over magnesium sulfate and concentrated. The crude was purified by treating with ether to give 0.62 g of 4-[3-(4-fluorophenyl)-1H-pyrazol-4-yl]-2-pyridinecarboxylic acid as a white solid (73% yield), mp: 245° C. (dec). Anal Calc'd for C15H10FN3O+0.2 H2O: C, 62.80; H, 3.65; N, 14.65. Found: C, 62.77; H, 3.42; N, 14,58.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 10 hours
  3. customAfter the removal of solvent
  4. dissolutionthe residue was dissolved in water
  5. extractionThen the aqueous phase was extracted with ethyl acetate
  6. dry with materialthe organic phase was dried over magnesium sulfate
  7. concentrationconcentrated
  8. customThe crude was purified
  9. additionby treating with ether

Sources & evidence

ORD record
ord-921dbc232a2141aa8b536cfbd0a60f74
Source dataset
uspto-grants-2006_07
Patent number
US07071198B1

Reaction notes

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