Diethyl Malonate → HCID 779729, compound

HRID 1106263Notes

Reaction equation

HRID 1106263 reaction equation
[C:1]([O:9]CC)(=O)[CH2:2][C:3]([O:5]CC)=O.[Na].[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([NH:20][NH2:21])=[CH:16][CH:15]=1>C(O)C>[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([N:20]2[C:1](=[O:9])[CH2:2][C:3](=[O:5])[NH:21]2)=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 7761Diethyl MalonateHCID 70624(4-Chlorophenyl)hydrazineHCID 5360545Sodium

Product 1

HCID 779729HCID 779729, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The starting material is prepared as follows: 20.0 g of diethyl malonate are added to 5.8 g of sodium metal dissolved in 100 ml of absolute ethanol. After stirring for 15 minutes, 17.8 g of p-chlorophenylhydrazine are added, and the resulting mixture is stripped to remove excess ethanol. The residue is heated at 110° to 120° for 4.5 hours, then quenched with 500 ml of ice-water. The resulting mixture is washed twice with diethyl ether and the aqueous layer is acidified with conc. hydrochloric acid to a pH below 2. The resulting solid is recrystallized from toluene, to give the 1-(p-chlorophenyl)-pyrazolidin-3,5-dione melting at 189°-193°.

Workup

  1. customThe starting material is prepared
  2. customto remove excess ethanol
  3. temperatureThe residue is heated at 110° to 120° for 4.5 hours
  4. customquenched with 500 ml of ice-water
  5. washThe resulting mixture is washed twice with diethyl ether
  6. customThe resulting solid is recrystallized from toluene

Sources & evidence

ORD record
ord-d1926827e8154e86aa928c9613fe108e
Source dataset
uspto-grants-1982_01
Patent number
US04312870

Reaction notes

Loading…