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

HRID 126999Notes

Reaction equation

HRID 126999 reaction equation
[OH-].[K+].[N:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9](=O)[CH:10]=[CH:11][C:12]([OH:14])=[O:13].[NH2:16][NH2:17]>CO>[N:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH2:10][CH:11]([C:12]([OH:14])=[O:13])[NH:17][N:16]=1

Participants

5

Reactant 3

HCID 9321HydrazineHCID 14797Potassium HydroxideHCID 541116954-(2-Pyridyl)-4-oxo-2-butenoic acid

Product 1

HCID 20288728(+/-)-3-(2-Pyridyl)-4,5-dihydro-1H-pyrazole-5-carboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Potassium hydroxide (3.29 g) is dissolved in 250 ml of methanol and 8.85 g of 4-(2-pyridyl)-4-oxo-2-butenoic acid is added. Hydrazine (1.6 g) is then added and the solution is heated at reflux temperature for 5 hours. Solvent is removed in vacuo and the residue is dissolved in 50 ml of water and treated with 3.0 g of acetic acid yielding the title compound.

Workup

  1. temperaturethe solution is heated
  2. temperatureat reflux temperature for 5 hours
  3. customSolvent is removed in vacuo
  4. dissolutionthe residue is dissolved in 50 ml of water
  5. additiontreated with 3.0 g of acetic acid yielding the title compound

Sources & evidence

ORD record
ord-8f70dbb555ac48049865387021afceae
Source dataset
uspto-grants-1981_03
Patent number
US04254267

Reaction notes

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