Hydrochloric Acid → 1-(5-Fluoropyridin-2-yl)-3-phenyl-1H-pyrazole-4-carboxylic acid

HRID 1842565Notes

Reaction equation

HRID 1842565 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH:12]=[C:11]([C:13]([O:15]C)=[O:14])[C:10]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[N:9]2)=[N:6][CH:7]=1.[OH-].[Na+:24].[ClH:25]>CO.C1COCC1>[Cl-:25].[Na+:24].[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH:12]=[C:11]([C:13]([OH:15])=[O:14])[C:10]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)=[N:9]2)=[N:6][CH:7]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 66679523Methyl 1-(5-fluoropyridin-2-yl)-3-phenyl-1H-pyrazole-4-carboxylate

Product 2

HCID 5234Sodium ChlorideHCID 666794871-(5-Fluoropyridin-2-yl)-3-phenyl-1H-pyrazole-4-carboxylic acidYield 146.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of methyl 1-(5-fluoropyridin-2-yl)-3-phenyl-1H-pyrazole-4-carboxylate (0.55 g, 1.86 mmol) in methanol (9.3 mL) and THF (9.3 mL) was added NaOH (1.0 M in water; 5.59 mL, 5.59 mmol). The mixture was stirred at 50° C. After 18 h, the mixture was cooled to ambient temperature and HCl (6.0 M in water; 0.93 mL, 5.59 mmol) was added. The mixture was concentrated to dryness to give sodium chloride salt of the title compound (0.77 g). MS 284.1 (M+1).

Workup

  1. temperaturethe mixture was cooled to ambient temperature
  2. concentrationThe mixture was concentrated to dryness

Sources & evidence

ORD record
ord-9a0b8ea3c5944dd998fb1c0772887021
Source dataset
uspto-grants-2015_02
Patent number
US08946231B2

Reaction notes

Loading…