Hydrochloric Acid → 3-(1,5-DIMETHYL-1H-PYRAZOL-4-YL)-ACRYLIC ACID

HRID 30680Notes

Reaction equation

HRID 30680 reaction equation
[CH3:1][N:2]1[C:6]([CH3:7])=[C:5](/[CH:8]=[CH:9]/[C:10]([O:12]CC)=[O:11])[CH:4]=[N:3]1.[OH-].[Na+].Cl>CO>[CH3:1][N:2]1[C:6]([CH3:7])=[C:5](/[CH:8]=[CH:9]/[C:10]([OH:12])=[O:11])[CH:4]=[N:3]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 83766845ethyl (2E)-3-(1,5-dimethyl-1H-pyrazol-4-yl)acrylate

Product 1

HCID 53740613-(1,5-DIMETHYL-1H-PYRAZOL-4-YL)-ACRYLIC ACIDYield 87%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

To a mixture of ethyl (2E)-3-(1,5-dimethyl-1H-pyrazol-4-yl)acrylate (380 mg) and methanol (20 ml) was added a 2N aqueous sodium hydroxide solution (2.0 ml), and the mixture was stirred at 60° C. for 14 hrs. 1N Hydrochloric acid was poured into the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated. Recrystallization of the residue from ethyl acetate-hexane gave (2E)-3-(1,5-dimethyl-1H-pyrazol-4-yl)acrylic acid (283 mg, 87%) as colorless prism crystals. melting point: 217-219° 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. customRecrystallization of the residue from ethyl acetate-hexane

Sources & evidence

ORD record
ord-91129ba6995c4c1d98c84d0f73224267
Source dataset
uspto-grants-2008_09
Patent number
US07423159B2

Reaction notes

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