Sodium Hydroxide → 5-(4-Fluorophenyl)-1-(6-methoxy-3-pyridyl)pyrazole-3-carboxylic acid

HRID 1437255Notes

Reaction equation

HRID 1437255 reaction equation
[OH-].[Na+].C([O:5][C:6]([C:8]1[CH:12]=[C:11]([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)[N:10]([C:20]2[CH:21]=[N:22][C:23]([O:26][CH3:27])=[CH:24][CH:25]=2)[N:9]=1)=[O:7])C>CO>[F:19][C:16]1[CH:17]=[CH:18][C:13]([C:11]2[N:10]([C:20]3[CH:21]=[N:22][C:23]([O:26][CH3:27])=[CH:24][CH:25]=3)[N:9]=[C:8]([C:6]([OH:7])=[O:5])[CH:12]=2)=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 579406805-(4-Fluorophenyl)-1-(6-methoxy-3-pyridyl)pyrazole-3-carboxylic acid ethyl ester

Product 1

HCID 230904085-(4-Fluorophenyl)-1-(6-methoxy-3-pyridyl)pyrazole-3-carboxylic acidYield 88%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Aqueous 1N sodium hydroxide (1.2 L) was added to 5-(4-fluorophenyl)-1-(6-methoxy-3-pyridyl)pyrazole-3-carboxylic acid ethyl ester (164 g) in methanol (1.6 L), and the resultant mixture was stirred at room temperature for 5 hours. The reaction solvent was removed under reduced pressure, and the residue was partitioned between water and diethyl ether. The aqueous layer was adjusted at pH 2 through addition of aqueous 1N hydrochloric acid (1.5 L), and the precipitated crystals were dissolved in chloroform. The resultant solution was partitioned by use of saturated brine, and the organic layer was dried over sodium sulfate anhydrate, followed by filtration. The solvent was evaporated under reduced pressure, and the precipitated crystals from diethyl ether were recovered by filtration, to thereby give the title compound (132.0 g, 88%).

Workup

  1. customThe reaction solvent was removed under reduced pressure
  2. customthe residue was partitioned between water and diethyl ether
  3. additionThe aqueous layer was adjusted at pH 2 through addition of aqueous 1N hydrochloric acid (1.5 L)
  4. dissolutionthe precipitated crystals were dissolved in chloroform
  5. customThe resultant solution was partitioned by use of saturated brine
  6. dry with materialthe organic layer was dried over sodium sulfate anhydrate
  7. filtrationfollowed by filtration
  8. customThe solvent was evaporated under reduced pressure
  9. filtrationthe precipitated crystals from diethyl ether were recovered by filtration

Sources & evidence

ORD record
ord-5af91f7dd39b417bbec58d5fd75312c4
Source dataset
uspto-grants-2009_11
Patent number
US07622471B2

Reaction notes

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