Ethanol → 1-(6-Chloro-2-pyridyl)pyrazolidin-3-one

HRID 582273Notes

Reaction equation

HRID 582273 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][NH2:9])[CH:5]=[CH:4][CH:3]=1.[O-:10][CH2:11][CH3:12].[Na+].[CH2:14](O)C>C1(C)C=CC=CC=1>[Cl:1][C:2]1[N:7]=[C:6]([N:8]2[CH2:14][CH2:12][C:11](=[O:10])[NH:9]2)[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 3200042-Chloro-6-hydrazinopyridineHCID 2723922Sodium ethoxide

Product 1

HCID 544652721-(6-Chloro-2-pyridyl)pyrazolidin-3-one

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 20.1 g (140 mmol) of 6-chloro-2-pyridylhydrazine (synthesis: Chem. Ber. 103. (1970) 1960) are added dropwise at 15°-20° C. to a mixture of 12.4 g (182 mmol) of sodium ethoxide, 100 ml of ethanol and 100 ml of toluene. After stirring for 2 hours at 25° C., the reaction mixture is evaporated, the residue is taken up in water and extracted with MTBE. The aqueous phase is adjusted to a pH of 6.5 and cooled to 5° C. The precipitate formed is filtered off and dried under reduced pressure at 40° C.

Workup

  1. customthe reaction mixture is evaporated
  2. extractionextracted with MTBE
  3. temperaturecooled to 5° C
  4. customThe precipitate formed
  5. filtrationis filtered off
  6. customdried under reduced pressure at 40° C.

Sources & evidence

ORD record
ord-edbf18bea0d64bdf8b2f75579af67ed2
Source dataset
uspto-grants-1999_07
Patent number
US05922886

Reaction notes

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