Methylhydrazine → HCID 178498595, compound

HRID 1378664Notes

Reaction equation

HRID 1378664 reaction equation
[C:1]([C:7]([O:9]C)=O)#[C:2][C:3]([O:5][CH3:6])=[O:4].[CH3:11][NH:12][NH2:13]>CCOCC>[CH3:6][O:5][C:3]([C:2]1[CH:1]=[C:7]([OH:9])[N:12]([CH3:11])[N:13]=1)=[O:4]

Participants

4

Reactant 2

HCID 6061MethylhydrazineHCID 12980Dimethyl acetylenedicarboxylate

Product 1

HCID 178498595HCID 178498595, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
-5 °C

Procedure

102.3 g (0.72 mol) dimethyl acetylenedicarboxylate was added to 1000 ml ether and cooled to -5° C. in an ice-methanol bath. 33 g (0.72 mol) Methylhydrazine in 100 ml ether was added dropwise so that the inner temperature did not rise above 0° C. The mixture was stirred for 1 hour at 0° C., the precipitate filtered off, washed with ether and dried in vacuo at 40° C. The intermediate was immersed for 10 minutes in an oil bath heated to 120° C. The reduction product was recrystallised from methanol.

Workup

  1. customdid not rise above 0° C
  2. filtrationthe precipitate filtered off
  3. washwashed with ether
  4. customdried in vacuo at 40° C
  5. waitThe intermediate was immersed for 10 minutes in an oil bath
  6. temperatureheated to 120° C
  7. customThe reduction product was recrystallised from methanol

Sources & evidence

ORD record
ord-6fc30bde42014c7c93d5e896b353ab62
Source dataset
uspto-grants-1997_09
Patent number
US05668278

Reaction notes

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