1,2-Dimethylhydrazine → 3-Hydroxy-1,2,4-trimethyl-5-pyrazolone

HRID 1903776Notes

Reaction equation

HRID 1903776 reaction equation
[CH3:1][CH:2]([C:8]([O:10]CC)=O)[C:3](OCC)=[O:4].[CH3:13][NH:14][NH:15][CH3:16].C[O-].[Na+]>CO>[OH:10][C:8]1[N:14]([CH3:13])[N:15]([CH3:16])[C:3](=[O:4])[C:2]=1[CH3:1]

Participants

5

Reactant 3

HCID 13221,2-DimethylhydrazineHCID 11857Diethyl methylmalonateHCID 10942334Sodium Methoxide

Product 1

HCID 128188533-Hydroxy-1,2,4-trimethyl-5-pyrazolone

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Diethyl methylmalonate and N,N'-dimethylhydrazine are heated under reflux for 170 hours in methanol in the presence of sodium methylate under an atmosphere of nitrogen. 3-Hydroxy-1,2,4-trimethyl-5-pyrazolone is obtained in the form of colorless crystals which, after recrystallization from ethyl acetate, melt at 87°-89° C.

Sources & evidence

ORD record
ord-ac6e86f114b546068b11630d63ef802c
Source dataset
uspto-grants-1984_03
Patent number
US04438128

Reaction notes

Loading…