Sodium Hydroxide → HCID 86692504, compound

HRID 1748557Notes

Reaction equation

HRID 1748557 reaction equation
C([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]([C:12]2[C:17]([F:18])=[CH:16][C:15]([C:19]([F:22])([F:21])[F:20])=[CH:14][N:13]=2)[C:10]=1[CH3:11])=[O:5])C.[OH-].[Na+]>O1CCCC1>[F:18][C:17]1[C:12]([N:9]2[C:10]([CH3:11])=[C:6]([C:4]([OH:5])=[O:3])[CH:7]=[N:8]2)=[N:13][CH:14]=[C:15]([C:19]([F:22])([F:20])[F:21])[CH:16]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86692473HCID 86692473, compound

Product 1

HCID 86692504HCID 86692504, compoundYield 85.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-[3-fluoro-5-(trifluoromethyl)pyridin-2-yl]-5-methyl-1H-pyrazole-4-carboxylic acid ethyl ester (2.17 g) in tetrahydrofuran (10 ml) was added 1 N aqueous solution of sodium hydroxide (10 ml), and stirred at room temperature overnight. After completion of the reaction, the organic solvent was evaporated in vacuo, then water and diethyl ether were added thereto, and the aqueous layer was separated. To the aqueous layer was added 1 N hydrochloric acid aqueous solution under ice-cooling to adjust the layer to pH 5, the precipitated solid was collected by filtration, and dried at 60° C. under air blow to give the titled compound (1.7 g) as a white solid. MS (ESI) m/z: 290 (M+H)+.

Workup

  1. customAfter completion of the reaction
  2. customthe organic solvent was evaporated in vacuo
  3. additionwater and diethyl ether were added
  4. customthe aqueous layer was separated
  5. additionTo the aqueous layer was added 1 N hydrochloric acid aqueous solution under ice-
  6. temperaturecooling
  7. filtrationthe precipitated solid was collected by filtration
  8. customdried at 60° C. under air blow

Sources & evidence

ORD record
ord-70cdd2f853f5418180de7090c7877b95
Source dataset
uspto-grants-2015_10
Patent number
US09150555B2

Reaction notes

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