Hydrazine hydrate (1:1) → 3(2H)-Pyridazinone, 6-(2-methyl-1H-imidazol-1-yl)-, hydrazone

HRID 434621Notes

Reaction equation

HRID 434621 reaction equation
Cl[C:2]1[N:3]=[N:4][C:5]([N:8]2[CH:12]=[CH:11][N:10]=[C:9]2[CH3:13])=[CH:6][CH:7]=1.O.[NH2:15][NH2:16]>>[NH:15]([C:2]1[N:3]=[N:4][C:5]([N:8]2[CH:12]=[CH:11][N:10]=[C:9]2[CH3:13])=[CH:6][CH:7]=1)[NH2:16]

Participants

3

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 126988723-Chloro-6-(2-methyl-1H-imidazol-1-yl)pyridazine

Product 1

HCID 30589113(2H)-Pyridazinone, 6-(2-methyl-1H-imidazol-1-yl)-, hydrazone

Procedure

6.7 g (35 millimoles) of 3-chloro-6-(2-methyl-imidazol-1-yl)-pyridazine are taken up in 30 ml of hydrazine hydrate and the mixture is heated for 5-10 hours at 100°-130° C. under nitrogen as a protective gas; the reaction mixture becomes homogeneous in the course of the first few hours. When the mixture has cooled, the crude product which has precipitated is filtered off. It is also possible to pour the reaction mixture into ice water and extract the mixture repeatedly with methylene chloride. Continuous extraction by means of a rotary perforator, using methylene chloride or chloroform as the extraction solvents, has also proved an advantageous method. Yet a further possibility is to distil off the hydrazine hydrate under reduced pressure.

Workup

  1. temperaturethe mixture is heated for 5-10 hours at 100°-130° C. under nitrogen as a protective gas
  2. temperatureWhen the mixture has cooled
  3. customthe crude product which has precipitated
  4. filtrationis filtered off
  5. additionto pour the reaction mixture into ice water
  6. extractionextract the mixture repeatedly with methylene chloride
  7. extractionContinuous extraction by means of a rotary perforator
  8. customto distil off the hydrazine hydrate under reduced pressure

Sources & evidence

ORD record
ord-be46844cd1424b5aa3394f373e3ea7dd
Source dataset
uspto-grants-1983_08
Patent number
US04399137

Reaction notes

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