Hydrazinecarboxaldehyde → HCID 12726830, compound

HRID 1764647Notes

Reaction equation

HRID 1764647 reaction equation
Cl[C:2]1[N:3]=[N:4][C:5]([C:8]2[CH:9]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:11]=[CH:12][CH:13]=2)=[CH:6][CH:7]=1.[CH:18]([NH:20][NH2:21])=O>C(O)CCC>[F:15][C:14]([F:17])([F:16])[C:10]1[CH:11]=[CH:12][CH:13]=[C:8]([C:5]2[CH:6]=[CH:7][C:2]3[N:3]([CH:18]=[N:20][N:21]=3)[N:4]=2)[CH:9]=1

Participants

4

Reactant 2

HCID 12229HydrazinecarboxaldehydeHCID 124495523-Chloro-6-[3-(trifluoromethyl)phenyl]pyridazine

Product 1

HCID 12726830HCID 12726830, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of 6.0 g. of 3-chloro-6-(α,α,α-trifluoro-m-tolyl)pyridazine (prepared as in Example 10), 2.78 g. of formylhydrazine and 75 ml. of butyl alcohol is allowed to stir at reflux temperature for 48 hours. The reaction mixture is concentrated free of solvent and the residue is dissolved in ethyl alcohol, treated with activated charcoal and filtered. The filtrate is cooled in an ice bath and the cream colored solid is collected. The solid is heated with diethyl ether and the mixture is filtered. The solid is recrystallized from ethyl acetate to afford the product of the example as cream colored crystals, m.p. 140°-143° C.

Workup

  1. additionA mixture of 6.0 g
  2. temperatureat reflux temperature for 48 hours
  3. concentrationThe reaction mixture is concentrated free of solvent
  4. dissolutionthe residue is dissolved in ethyl alcohol
  5. additiontreated with activated charcoal
  6. filtrationfiltered
  7. temperatureThe filtrate is cooled in an ice bath
  8. customis collected
  9. temperatureThe solid is heated with diethyl ether
  10. filtrationthe mixture is filtered
  11. customThe solid is recrystallized from ethyl acetate
  12. customto afford the product of the example as cream colored crystals, m.p. 140°-143° C.

Sources & evidence

ORD record
ord-28cf0c6f6abc4b12bc44224bf17ee68e
Source dataset
uspto-grants-1978_09
Patent number
US04117130

Reaction notes

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