Sodium ethoxide → Ethyl 5-oxo-2-(pyridin-3-yl)pyrazolidine-3-carboxylate

HRID 517365

Reaction equation

HRID 517365 reaction equation
[O-]CC.[Na+].[C:5]([O:14][CH2:15][CH3:16])(=[O:13])/[CH:6]=[CH:7]\[C:8]([O:10]CC)=O.[NH:17]([C:19]1[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=1)[NH2:18]>C(O)C>[O:10]=[C:8]1[NH:18][N:17]([C:19]2[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=2)[CH:6]([C:5]([O:14][CH2:15][CH3:16])=[O:13])[CH2:7]1

Participants

5

Reactant 3

HCID 2723922Sodium ethoxideHCID 5271566Diethyl MaleateHCID 109095193-Hydrazinopyridine

Product 1

HCID 118023220Ethyl 5-oxo-2-(pyridin-3-yl)pyrazolidine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In a preferred reaction, sodium ethoxide in an anhydrous ethanol are introduced into a reaction vessel and 3-hydrazinopyridine•dihydrochloride is added. The mixture is stirred and diethyl maleate is added. The mixture is heated at about 60° C. until most of the 3-hydrazinopyridine has reacted. The mixture is allowed to cool and the excess base is neutralized with acid. The crude ethyl 5-oxo-2-(pyridin-3-yl)pyrazolidine-3-carboxylate (10a) is conveniently isolated and purified by standard techniques.

Workup

  1. additionare introduced into a reaction vessel
  2. customhas reacted
  3. temperatureto cool

Sources & evidence

ORD record
ord-42d8946a0a5a4bf3931940a96bca62d0
Source dataset
uspto-grants-2015_08
Patent number
US09115115B1

Linked notes

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