Hydrazine hydrate (1:1) → HCID 55279275, compound

HRID 1524512Notes

Reaction equation

HRID 1524512 reaction equation
[Cl:1][C:2]1[N:3]=[N:4][C:5](Cl)=[C:6]([CH3:10])[C:7]=1[CH2:8][CH3:9].O.[NH2:13][NH2:14]>O1CCOCC1>[Cl:1][C:2]1[N:3]=[N:4][C:5]([NH:13][NH2:14])=[C:6]([CH3:10])[C:7]=1[CH2:8][CH3:9]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 57431053HCID 57431053, compound

Product 1

HCID 55279275HCID 55279275, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

3,6-Dichloro-4-ethyl-5-methylpyridazine (W4.007; 1 g) was initially charged in dioxane (8 ml) with addition of hydrazine monohydrate (2 ml) in a microwave vessel at RT. Thereafter, the reaction mixture was kept at 140° C. in the microwave for 1 h. In the course of standing overnight, a solid precipitated out, which was filtered off with suction, washed and dried. 345 mg of (6-chloro-5-ethyl-4-methylpyridazin-3-yl)hydrazine were obtained as the free base. The mother liquor was concentrated to dryness and the residue was purified by means of preparative HPLC (met. F). The product fractions, each of them clean, were combined, freed of the acetonitrile under reduced pressure and freeze-dried. 340 mg of 6-chloro-4-ethyl-5-methylpyridazin-3-yl)hydrazine trifluoroacetic acid salt and 239 mg of (6-chloro-5-ethyl-4-methylpyridazin-3-yl)hydrazine as the trifluoroacetate were obtained.

Workup

  1. waitIn the course of standing overnight
  2. customa solid precipitated out
  3. filtrationwhich was filtered off with suction
  4. washwashed
  5. customdried

Sources & evidence

ORD record
ord-9f12d6b2be414406a464aa35fa529c9b
Source dataset
uspto-grants-2015_07
Patent number
US09079906B2

Reaction notes

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