Hydrazinecarboxylic acid, ethyl ester → 3-(2-Carbethoxyhydrazino)-6-dimethylaminopyridazine hydrochloride

HRID 1414868Notes

Reaction equation

HRID 1414868 reaction equation
[Cl:1][C:2]1[N:3]=[N:4][C:5]([N:8]([CH3:10])[CH3:9])=[CH:6][CH:7]=1.[C:11]([NH:16][NH2:17])([O:13][CH2:14][CH3:15])=[O:12]>O>[ClH:1].[C:11]([NH:16][NH:17][C:2]1[N:3]=[N:4][C:5]([N:8]([CH3:10])[CH3:9])=[CH:6][CH:7]=1)([O:13][CH2:14][CH3:15])=[O:12]

Participants

4

Reactant 2

HCID 20064Hydrazinecarboxylic acid, ethyl esterHCID 2524746-chloro-N,N-dimethylpyridazin-3-amine

Product 1

HCID 214858913-(2-Carbethoxyhydrazino)-6-dimethylaminopyridazine hydrochloride

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of 1.57 g (0.01 moles) 3-chloro-6-dimethylaminopyridazine and 2.08 g (0.02 moles) monocarbethoxyhydrazine is warmed up for half an hour at 160° C. The resulting mixture is cooled, water added thereto, the solid which separates filtered away and the filtrate neutralized with NaHCO3 until a final pH 7. The mixture is then extracted with chloroform; the organic extract dried over sodium sulphate and the solvent evaporated. The residual oil is purified by chromatography on silica gel, eluting with a mixture of chloroform:methanol 8.5:1.5. The unitary fractions on thin layer chromatography with the same Rf are collected together, evaporated and the residue treated while warm with ethyl ether, and the residue filtered off. By addition of hydrogen chloride to the filtrate, 3-(2-carbethoxyhydrazino)-6-dimethylaminopyridazine hydrochloride precipitates with good yields melting at 215°-217° C (with dec).

Workup

  1. temperatureThe resulting mixture is cooled
  2. filtrationthe solid which separates filtered away
  3. extractionThe mixture is then extracted with chloroform
  4. extractionthe organic extract
  5. dry with materialdried over sodium sulphate
  6. customthe solvent evaporated
  7. customThe residual oil is purified by chromatography on silica gel
  8. washeluting with a mixture of chloroform:methanol 8.5:1.5
  9. customThe unitary fractions on thin layer chromatography with the same Rf are collected together
  10. customevaporated
  11. additionthe residue treated
  12. temperaturewhile warm with ethyl ether
  13. filtrationthe residue filtered off
  14. additionBy addition of hydrogen chloride to the filtrate, 3-(2-carbethoxyhydrazino)-6-dimethylaminopyridazine hydrochloride
  15. customprecipitates
  16. customwith good yields melting at 215°-217° C (with dec)

Sources & evidence

ORD record
ord-623fccde8f114c3e9ad17840c23ea92e
Source dataset
uspto-grants-1977_01
Patent number
US04002753

Reaction notes

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