Methylhydrazine → HCID 178481821, compound

HRID 972063Notes

Reaction equation

HRID 972063 reaction equation
[CH3:1][NH:2][NH2:3].C([O:6][C:7](=O)[CH2:8][C:9](=O)[C:10]([CH3:13])([CH3:12])[CH3:11])C.C[O-].[Na+]>CO>[CH3:1][N:2]1[C:7]([OH:6])=[CH:8][C:9]([C:10]([CH3:13])([CH3:12])[CH3:11])=[N:3]1

Participants

5

Reactant 3

HCID 6061MethylhydrazineHCID 86950Ethyl pivaloylacetateHCID 10942334Sodium Methoxide

Product 1

HCID 178481821HCID 178481821, compoundYield 87.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

9.2 g (0.2 mol) of methylhydrazine were added dropwise to a mixture of 34.4 g (0.2 mol) of pivaloylacetic acid ethyl ester, 10.8 g (0.2 mol) of sodium methylate and 100 ml of methanol at 20° C. When the exothermic reaction had subsided, the reaction mixture was heated for 2 hours under reflux and then concentrated, the residue was taken up in 200 ml of water and this solution was acidified with concentrated hydrochloric acid to a pH of ca. 6. The resulting precipitate was filtered off, dried and recrystallized from isopropanol. 27 g (87% of theory) of 1-methyl-3-tert.-butyl-5-hydroxy-pyrazole were obtained in the form of colorless crystals of melting point 150° C.

Workup

  1. customWhen the exothermic reaction
  2. temperaturethe reaction mixture was heated for 2 hours
  3. temperatureunder reflux
  4. concentrationconcentrated
  5. filtrationThe resulting precipitate was filtered off
  6. customdried
  7. customrecrystallized from isopropanol

Sources & evidence

ORD record
ord-26b3950ab89342d184c25e734689fdc1
Source dataset
uspto-grants-1979_07
Patent number
US04163052

Reaction notes

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