Methylhydrazine → Ethyl 2-(methylhydrazono)propanoate

HRID 2111109Notes

Reaction equation

HRID 2111109 reaction equation
[C:1]([O:6][CH2:7][CH3:8])(=[O:5])[C:2]([CH3:4])=O.[O-]S([O-])(=O)=O.[Mg+2].[CH3:15][NH:16][NH2:17]>C(Cl)(Cl)Cl>[CH3:15][NH:16][N:17]=[C:2]([CH3:4])[C:1]([O:6][CH2:7][CH3:8])=[O:5]

Participants

5

Reactant 3

HCID 6061MethylhydrazineHCID 12041Ethyl pyruvateHCID 24083Sulfuric acid magnesium salt (1:1)

Product 1

HCID 73828661Ethyl 2-(methylhydrazono)propanoateYield 94%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a suspension of ethyl pyruvate (37.8 mL, 338 mmol) and MgSO4 (40.8 g, 339 mmol) in CHCl3 (500 mL) was added a solution of methylhydrazine (18.0 mL, 332 mmol) in CHCl3 (100 mL) at 0° C. The reaction mixture was warmed to room temperature. After stirring for 24 hours at room temperature, the reaction mixture was filtered. The filtrate was concentrated under reduced pressure to give 44 g (94%) of the desired product that was used directly without further purification.

Workup

  1. filtrationthe reaction mixture was filtered
  2. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-735831e8bfe54cd68e3d53b60d3f07c0
Source dataset
uspto-grants-2009_04
Patent number
US07517994B2

Reaction notes

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