Methanol → HCID 58158461, compound

HRID 2095809Notes

Reaction equation

HRID 2095809 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12](=[O:13])[C:11]([C:14]([O:16]CC)=[O:15])=[CH:10][N:9]2[CH3:19])=[CH:4][CH:3]=1.CO.[OH-].[Na+]>O1CCCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:12](=[O:13])[C:11]([C:14]([OH:16])=[O:15])=[CH:10][N:9]2[CH3:19])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 58158460HCID 58158460, compound

Product 1

HCID 58158461HCID 58158461, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of ethyl 2-(4-fluorophenyl)-1-methyl-3-oxo-2,3-dihydro-1H-pyrazole-4-carboxylate (1.6 g, 5.9 mmol) in tetrahydrofuran (6 mL)/methanol (5 mL) was added 4N aqueous sodium hydroxide solution (9 mL), and the mixture was stirred at 60° C. for 1 hr. Tetrahydrofuran and methanol were evaporated under reduced pressure. 6N Aqueous hydrochloric acid solution was added to the residue with stirring, and the precipitated solid was collected by filtration. The filtrate was washed with water and ethyl acetate/hexane (1/5), and dried under reduced pressure to give the title compound (1.1 g, 79%) as a white solid.

Workup

  1. customTetrahydrofuran and methanol were evaporated under reduced pressure
  2. addition6N Aqueous hydrochloric acid solution was added to the residue
  3. stirringwith stirring
  4. filtrationthe precipitated solid was collected by filtration
  5. washThe filtrate was washed with water and ethyl acetate/hexane (1/5)
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-fb5e9d05bebc47ed879ef8f93003586f
Source dataset
uspto-grants-2013_05
Patent number
US08445509B2

Reaction notes

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