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Sodium Hydroxide → [3-Methyl-1-(4-methylpyridin-3-yl)-5-phenyl-1H-pyrazol-4-yl]acetic acid

HRID 888726
Notes
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Reaction equation

HRID 888726 reaction equation
[OH-].[Na+].[CH3:3][C:4]1[C:8]([CH2:9][C:10]([O:12]C)=[O:11])=[C:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:6]([C:20]2[CH:21]=[N:22][CH:23]=[CH:24][C:25]=2[CH3:26])[N:5]=1>CO>[CH3:3][C:4]1[C:8]([CH2:9][C:10]([OH:12])=[O:11])=[C:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:6]([C:20]2[CH:21]=[N:22][CH:23]=[CH:24][C:25]=2[CH3:26])[N:5]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86626934Methyl [3-methyl-1-(4-methylpyridin-3-yl)-5-phenyl-1H-pyrazol-4-yl]acetate

Product 1

HCID 68818330[3-Methyl-1-(4-methylpyridin-3-yl)-5-phenyl-1H-pyrazol-4-yl]acetic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
20 °C

Procedure

0.100 g (2.489 mmol) of 2 molar aqueous sodium hydroxide solution was added to 0.200 g (0.498 mmol) of methyl [3-methyl-1-(4-methylpyridin-3-yl)-5-phenyl-1H-pyrazol-4-yl]acetate in 5.00 ml of methanol, and the mixture was stirred at 20° C. for 1 h. The methanol was removed under reduced pressure, and the residue was poured onto a mixture of 10 ml of water and 15 ml of dichloromethane. The aqueous phase was extracted with 15 ml of dichloromethane, acidified with concentrated hydrochloric acid (pH=3) and extracted three times with in each case 15 ml of dichloromethane. Drying of the combined organic phases and removal of the solvent under reduced pressure give 0.108 g (71% of theory) of a yellow solid of melting point 246° C.

Workup

  1. customThe methanol was removed under reduced pressure
  2. additionthe residue was poured onto a mixture of 10 ml of water and 15 ml of dichloromethane
  3. extractionThe aqueous phase was extracted with 15 ml of dichloromethane
  4. extractionextracted three times with in each case 15 ml of dichloromethane
  5. customDrying of the combined organic phases and removal of the solvent under reduced pressure
  6. customgive 0.108 g (71% of theory) of a yellow solid of melting point 246° C.

Sources & evidence

ORD record
ord-a531c57b56a4410ca1282e9efbb24737
Source dataset
uspto-grants-2012_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08252723B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes