Diethyl Malonate → HCID 135713177, compound

HRID 2183582Notes

Reaction equation

HRID 2183582 reaction equation
[Na].[NH2:2][C:3]1[N:7]([CH3:8])[N:6]=[CH:5][C:4]=1[C:9]([O:11]CC)=O.[C:14](OCC)(=[O:21])[CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17]>C(O)C.O>[OH:11][C:9]1[C:4]2[CH:5]=[N:6][N:7]([CH3:8])[C:3]=2[NH:2][C:14](=[O:21])[C:15]=1[C:16]([O:18][CH2:19][CH3:20])=[O:17]

Participants

6

Reactant 3

HCID 7761Diethyl MalonateHCID 271299Ethyl 5-amino-1-methyl-1H-pyrazole-4-carboxylateHCID 5360545Sodium

Product 1

HCID 135713177HCID 135713177, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

A solution of sodium metal (12.7 g, 0.55 mol) in ethanol is treated at room temperature with ethyl 5-amino-1-methyl-4-pyrazolecarboxylate (25 g, 0.148 mol), stirred for 0.5 h, treated dropwise with a solution of diethyl malonate (80 mL, 0.52 mol in ethanol over a 0.5 h period, heated at reflux temperature for 56 h, cooled to room temperature, diluted with water, washed with ethyl acetate, acidified to pH 2 with HCl and filtered. The filtercake is washed sequentially with water, ethanol, ethyl acetate and toluene and dried in vacuo at 40° C. for 16 h to afford the title product as a white solid, 28.7 g (82% yield), identified by HNMR analysis.

Workup

  1. temperatureheated
  2. temperatureat reflux temperature for 56 h
  3. washwashed with ethyl acetate
  4. filtrationfiltered
  5. washThe filtercake is washed sequentially with water, ethanol, ethyl acetate and toluene
  6. customdried in vacuo at 40° C. for 16 h

Sources & evidence

ORD record
ord-bc9c7f39a1524ac492707d7b07498076
Source dataset
uspto-grants-2005_05
Patent number
US06900223B2

Reaction notes

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