Hydrazine → (+/-)-3-(2-Furanyl)-4,5-dihydro-1H-pyrazole-5-carboxylic acid

HRID 126988Notes

Reaction equation

HRID 126988 reaction equation
[OH-].[K+].[O:3]1[CH:7]=[CH:6][CH:5]=[C:4]1[C:8](=O)[CH:9]=[CH:10][C:11]([OH:13])=[O:12].[NH2:15][NH2:16]>CO>[O:3]1[CH:7]=[CH:6][CH:5]=[C:4]1[C:8]1[CH2:9][CH:10]([C:11]([OH:13])=[O:12])[NH:16][N:15]=1

Participants

5

Reactant 3

HCID 9321HydrazineHCID 14797Potassium HydroxideHCID 542490284-(2-Furanyl)-4-oxo-2-butenoic acid

Product 1

HCID 20288730(+/-)-3-(2-Furanyl)-4,5-dihydro-1H-pyrazole-5-carboxylic acidYield 66.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Potassium hydroxide (660 mg) is dissolved in 25 cc of methanol and 1.66 g of 4-(2-furanyl)-4-oxo-2-butenoic acid is added. Hydrazine (320 mg) is then added and the solution is refluxed for 2 hours. The methanol is removed and the viscous residue is dissolved in 50 cc of water. The solution is made strongly acid with 20% HCl and a precipitate forms. The solid is filtered quickly to yield 1.2 g of the title compound, melting point 185°-190° C., dec.

Workup

  1. temperaturethe solution is refluxed for 2 hours
  2. customThe methanol is removed
  3. dissolutionthe viscous residue is dissolved in 50 cc of water
  4. filtrationThe solid is filtered quickly

Sources & evidence

ORD record
ord-5194945f50a849d981f4a7b062dc0452
Source dataset
uspto-grants-1981_03
Patent number
US04254267

Reaction notes

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