Ethyl formate → HCID 178419957, compound

HRID 1725764Notes

Reaction equation

HRID 1725764 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][N:7]=[CH:6][CH:5]=1)(=O)[CH3:2].[CH:10](OCC)=O.C[O-].[Na+].Cl.Cl.[NH2:20][NH2:21].[OH-].[Na+]>C1C=CC=CC=1.O>[NH:20]1[CH:10]=[CH:2][C:1]([C:4]2[CH:9]=[CH:8][N:7]=[CH:6][CH:5]=2)=[N:21]1

Participants

8

Reactant 5

HCID 8025Ethyl formateHCID 142824-AcetylpyridineHCID 14798Sodium HydroxideHCID 17548Hydrazine, dihydrochlorideHCID 10942334Sodium Methoxide

Product 1

HCID 178419957HCID 178419957, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 962WaterSolvent

Procedure

To a mixture of 4-acetylpyridine (75 mL, 0.68 mol) and ethyl formate (109 mL) in anhydrous benzene (1 L) was added sodium methoxide (73 g) and the resulting mixture was refluxed for 18 hours. The mixture was cooled and benzene decanted from a sticky solid, which had formed during the reaction. The crude product was dissolved in water (700 mL) and hydrazine dihydrochloride was added and the resulting mixture was stirred at room temperature for 2 hours. The mixture was redissolved by addition of 5N NaOH. Precipitate formed which was removed by filtration and dried to give 4-(1H-pyrazol-3-yl)pyridine (35 g).

Workup

  1. temperaturethe resulting mixture was refluxed for 18 hours
  2. temperatureThe mixture was cooled
  3. custombenzene decanted from a sticky solid
  4. customwhich had formed during the reaction
  5. customPrecipitate formed which
  6. customwas removed by filtration
  7. customdried

Sources & evidence

ORD record
ord-bc64dc9165ff488ca48aa2e222543ee4
Source dataset
uspto-grants-2009_02
Patent number
US07491737B2

Reaction notes

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