Methylhydrazine → HCID 57442165, compound

HRID 2068915Notes

Reaction equation

HRID 2068915 reaction equation
O=[C:2]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:3]([O:5][CH2:6][CH3:7])=[O:4].[CH3:13][NH:14][NH2:15]>CCO>[CH3:13][NH:14][N:15]=[C:2]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:3]([O:5][CH2:6][CH3:7])=[O:4]

Participants

4

Reactant 2

HCID 6061MethylhydrazineHCID 691051,3-Diethyl 2-oxopropanedioate

Product 1

HCID 57442165HCID 57442165, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of diethyl ketomalonate (95 g, 546 mmol) in EtOH (600 mL) (2 L 3-neck flask equipped with thermocouple, N2 line, condenser and mechanical stirrer) was added MeNHNH2 (32 mL, 600 mmol) in one portion at room temperature. The reaction mixture was warmed to 60° C. (internal temperature, heated by a heating mantle) and stirred for 6 hours. The reaction mixture was cooled to room temperature and stirred overnight. The reaction mixture was concentrated under reduced pressure to give the crude material along with solid precipitates that was purified by a silica gel plug (3:2 hexanes:EtOAc) to afford 81 g (74%) of the desired product.

Workup

  1. temperatureheated by a heating mantle) and
  2. temperatureThe reaction mixture was cooled to room temperature
  3. stirringstirred overnight
  4. concentrationThe reaction mixture was concentrated under reduced pressure
  5. customto give the crude material along with solid
  6. customprecipitates that
  7. customwas purified by a silica gel plug (3:2 hexanes:EtOAc)

Sources & evidence

ORD record
ord-4530c5876786424eacd06377d30b7bb7
Source dataset
uspto-grants-2012_10
Patent number
US08299076B2

Reaction notes

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