Methylhydrazine → HCID 178499537, compound

HRID 1973246Notes

Reaction equation

HRID 1973246 reaction equation
[CH3:1][NH:2][NH2:3].[CH3:4][C:5]([CH:7]([C:12]([O:14][CH3:15])=[O:13])C(OC)=O)=O.[CH3:16][O-:17].[Na+]>CO>[CH3:1][N:2]1[C:16]([OH:17])=[CH:4][C:5]([CH2:7][C:12]([O:14][CH3:15])=[O:13])=[N:3]1

Participants

5

Reactant 3

HCID 6061MethylhydrazineHCID 568068HCID 568068, compoundHCID 10942334Sodium Methoxide

Product 1

HCID 178499537HCID 178499537, compoundYield 35.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

23 g of monomethylhydrazine were added to 87 g (0.5 mole) of acetonedicarboxylic acid dimethyl ester in 200 ml of methanol, during which the reaction temperature rose to 65° C. After completion of the addition, the mixture was stirred for a further 2 hours and 0.5 mole of sodium methylate in methanol was then added. The reaction was slightly exothermic. The reaction mixture was stirred for a further 2 hours and evaporated, and the residue was dissolved in water. After acidification with glacial acetic acid, the precipitate was filtered off, dried and recrystallized from an ethyl acetate/acetonitrile mixture. 30 g (35% of theory) of 1-methyl-3-methoxycarbonylmethyl-5-hydroxypyrazole of melting point 148° C were obtained. ##SPC7##

Workup

  1. customrose to 65° C
  2. additionAfter completion of the addition
  3. stirringThe reaction mixture was stirred for a further 2 hours
  4. customevaporated
  5. dissolutionthe residue was dissolved in water
  6. filtrationAfter acidification with glacial acetic acid, the precipitate was filtered off
  7. customdried
  8. customrecrystallized from an ethyl acetate/acetonitrile mixture

Sources & evidence

ORD record
ord-50b36f5c167f4708b8ac6d5338e7bc9c
Source dataset
uspto-grants-1976_12
Patent number
US03996367

Reaction notes

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