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

HRID 571000

Reaction equation

HRID 571000 reaction equation
[O-]CC.[Na+].Cl.Cl.[NH:7]([C:9]1[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=1)[NH2:8].[C:15](OCC)(=[O:23])/[CH:16]=[CH:17]\[C:18]([O:20][CH2:21][CH3:22])=[O:19].N(C1C=NC=CC=1)N>C(O)C>[O:23]=[C:15]1[NH:8][N:7]([C:9]2[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=2)[CH:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:16]1

Participants

6

Reactant 4

HCID 2723922Sodium ethoxideHCID 5271566Diethyl MaleateHCID 109095193-HydrazinopyridineHCID 171324893-Hydrazinylpyridine dihydrochloride

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-973a67849011439b9851380da46bdb5c
Source dataset
uspto-grants-2015_05
Patent number
US09024031B1

Linked notes

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