Hydrochloric Acid → (2E)-3-[1-Methyl-5-(2-thienyl)-1H-pyrazol-4-yl]-2-propenoic acid

HRID 30676Notes

Reaction equation

HRID 30676 reaction equation
[CH3:1][N:2]1[C:6]([C:7]2[S:8][CH:9]=[CH:10][CH:11]=2)=[C:5](/[CH:12]=[CH:13]/[C:14]([O:16]CC)=[O:15])[CH:4]=[N:3]1.[OH-].[Na+].Cl>CO>[CH3:1][N:2]1[C:6]([C:7]2[S:8][CH:9]=[CH:10][CH:11]=2)=[C:5](/[CH:12]=[CH:13]/[C:14]([OH:16])=[O:15])[CH:4]=[N:3]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86602518HCID 86602518, compound

Product 1

HCID 69205478(2E)-3-[1-Methyl-5-(2-thienyl)-1H-pyrazol-4-yl]-2-propenoic acidYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

To a mixture of ethyl (2E)-3-[1-methyl-5-(2-thienyl)-1H-pyrazol-4-yl]acrylate (2.0 g) and methanol (20 ml) was added 2N aqueous sodium hydroxide solution (7.6 ml) and the mixture was stirred at 60° C. for 30 min. 1N Hydrochloric acid was poured into the reaction mixture, and the precipitated solids were collected by filtration, washed with water and dried with airflow to give (2E)-3-[1-methyl-5-(2-thienyl)-1H-pyrazol-4-yl]acrylic acid (1.69 g, 95%) as crystals. Recrystallization thereof from methanol-isopropyl ether gave colorless prism crystals. melting point: 210-212° C.

Workup

  1. filtrationthe precipitated solids were collected by filtration
  2. washwashed with water
  3. customdried with airflow

Sources & evidence

ORD record
ord-de128edeeb284892846d727b09e40b32
Source dataset
uspto-grants-2008_09
Patent number
US07423159B2

Reaction notes

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