Citric Acid → (2E)-3-[1-methyl-5-(3-pyridinyl)-1H-pyrazol-4-yl]acrylic acid

HRID 30678Notes

Reaction equation

HRID 30678 reaction equation
[CH3:1][N:2]1[C:6]([C:7]2[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=2)=[C:5](/[CH:13]=[CH:14]/[C:15]([O:17]CC)=[O:16])[CH:4]=[N:3]1.[OH-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CO>[CH3:1][N:2]1[C:6]([C:7]2[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=2)=[C:5](/[CH:13]=[CH:14]/[C:15]([OH:17])=[O:16])[CH:4]=[N:3]1

Participants

5

Reactant 3

HCID 311Citric AcidHCID 14798Sodium HydroxideHCID 86602519HCID 86602519, compound

Product 1

HCID 69208696(2E)-3-[1-methyl-5-(3-pyridinyl)-1H-pyrazol-4-yl]acrylic acidYield 47.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

To a mixture of ethyl (2E)-3-[1-methyl-5-(3-pyridinyl)-1H-pyrazol-4-yl]acrylate (700 mg) and methanol (5 ml) was added a 2N aqueous sodium hydroxide solution (2.7 ml) and the mixture was stirred at 40° C. for 14 hrs. A saturated aqueous citric acid solution was poured into the reaction mixture to adjust pH to 5, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated. The residue was recrystallized from ethyl acetate-isopropyl ether to give (2E)-3-[1-methyl-5-(3-pyridinyl)-1H-pyrazol-4-yl]acrylic acid (296 mg, 47%) as pale-yellow prism crystals. melting point: 236-237° C.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was recrystallized from ethyl acetate-isopropyl ether

Sources & evidence

ORD record
ord-2d639f25036d4b7292d05d9e76b38452
Source dataset
uspto-grants-2008_09
Patent number
US07423159B2

Reaction notes

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