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Methanol → 2-(5-oxo-2,5-dihydro-1H-pyrazol-3-yl)acetic acid

HRID 606521
Notes
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Reaction equation

HRID 606521 reaction equation
[O:1]=[C:2]1[NH:6][NH:5][C:4]([CH2:7][C:8]([O:10]CC)=[O:9])=[CH:3]1.CO.O.[OH-].[Na+]>C1COCC1>[O:1]=[C:2]1[NH:6][NH:5][C:4]([CH2:7][C:8]([OH:10])=[O:9])=[CH:3]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 14798Sodium HydroxideHCID 43831447ethyl (5-oxo-2,5-dihydro-1H-pyrazol-3-yl)acetate

Product 1

HCID 167653152-(5-oxo-2,5-dihydro-1H-pyrazol-3-yl)acetic acidYield 82%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Conditions

Temperature
80 °C

Procedure

To a suspension of ethyl (5-oxo-2,5-dihydro-1H-pyrazol-3-yl)acetate obtained in Reference Example 117 (5.00 g, 29.4 mmol) in THF (20 mL)-methanol (20 mL)-water (20 mL) was added 5N aqueous sodium hydroxide solution (11.0 mL, 88.0 mmol) at room temperature, and the mixture was stirred under heating at 80° C. for 3 hr. The reaction mixture allowed to cool to room temperature, and concentrated under reduced pressure, and the residue was diluted with water, and acidified with 6N hydrochloric acid. The precipitated solid was collected by filtration, and washed with water, and dried under nitrogen stream to give the title compound as a white powder (3.43 g, 82%).

Workup

  1. temperatureto cool to room temperature
  2. concentrationconcentrated under reduced pressure
  3. additionthe residue was diluted with water
  4. filtrationThe precipitated solid was collected by filtration
  5. washwashed with water
  6. customdried under nitrogen stream

Sources & evidence

ORD record
ord-6de0b517e36f403b8d8c09f3adb76c16
Source dataset
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07915267B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes