Hydrazine hydrate (1:1) → HCID 54138370, compound

HRID 657917Notes

Reaction equation

HRID 657917 reaction equation
[Cl:1][C:2]1[N:3]=[N:4][C:5]([Cl:10])=[CH:6][C:7]=1[CH2:8][CH3:9].O.[NH2:12][NH2:13]>O1CCOCC1>[Cl:10][C:5]1[N:4]=[N:3][C:2]([NH:12][NH2:13])=[C:7]([CH2:8][CH3:9])[CH:6]=1.[Cl:1][C:2]1[N:3]=[N:4][C:5]([NH:12][NH2:13])=[CH:6][C:7]=1[CH2:8][CH3:9]

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 140241633,6-Dichloro-4-ethylpyridazine

Product 2

HCID 54138370HCID 54138370, compoundHCID 58046013HCID 58046013, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

3,6-Dichloro-4-ethylpyridazine (W4.003, 2×2.4 g) was divided between 2 microwave vessels and each was admixed with a mixture of hydrazine monohydrate (6 ml) and dioxane (7 ml). The reaction mixture was kept in the microwave at 130° C. for 1 h. Subsequently, the contents of the two vessels were combined in a round-bottom flask and dried. The residue was admixed with water and extracted three times with dichloromethane. The combined organic phases were dried over sodium sulfate and, after the desiccant had been filtered off, dried under reduced pressure. The workup process was repeated twice more. The residue thus obtained was separated by means of preparative HPLC (method A, except gradient of 100% water+0.05% TFA→15% acetonitrile/85% water+0.05% TFA in 25 min). The product fractions, each of them clean, were combined, freed of the acetonitrile under reduced pressure and freeze-dried. 1.35 g of (6-chloro-4-ethylpyridazin-3-yl)hydrazine as the trifluoroacetate and 3.96 g of (6-chloro-5-ethylpyridazin-3-yl)hydrazine as the trifluoroacetate were obtained.

Workup

  1. customSubsequently, the contents of the two vessels were combined in a round-bottom flask
  2. customdried
  3. extractionextracted three times with dichloromethane
  4. dry with materialThe combined organic phases were dried over sodium sulfate
  5. filtrationafter the desiccant had been filtered off
  6. customdried under reduced pressure
  7. customThe residue thus obtained
  8. customwas separated by means of preparative HPLC (method A, except gradient of 100% water+0.05% TFA→15% acetonitrile/85% water+0.05% TFA in 25 min)
  9. customfreeze-dried

Sources & evidence

ORD record
ord-2e6981fd3b21436e956198b086b4dec7
Source dataset
uspto-grants-2011_12
Patent number
US08076336B2

Reaction notes

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