Hydrazinecarboxaldehyde → HCID 20310369, compound

HRID 1763621Notes

Reaction equation

HRID 1763621 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:11]=[CH:12][C:13](=O)[NH:14][N:15]=2)=[CH:6][C:5]=1[C:17]([F:20])([F:19])[F:18])([O-:3])=[O:2].P(Cl)(Cl)(Cl)=O.Cl[C:27]1[N:28]=[N:29]C(C2C=CC([N+]([O-])=O)=C(C(F)(F)F)C=2)=CC=1.C(NN)=O>C(O)CCC>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:11]=[CH:12][C:13]3[N:14]([CH:27]=[N:28][N:29]=3)[N:15]=2)=[CH:6][C:5]=1[C:17]([F:20])([F:19])[F:18])([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 12229HydrazinecarboxaldehydeHCID 24813Phosphorus oxychlorideHCID 20310370HCID 20310370, compoundHCID 20310387HCID 20310387, compound

Product 1

HCID 20310369HCID 20310369, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of 7.0 g. of 6-[4-nitro-3-(trifluoromethyl)phenyl]-3(2H)-pyridazinone and 80 ml. of phosphorus oxychloride is heated on a steam bath for 18 hours. The solvent is removed and ice water added to the residue. Filtration gives 7.2 g. of 3-chloro-6-[4-nitro-3-(trifluoromethyl)phenyl]pyridazine as tan crystals, m.p. 129°-135° C. Recrystallization from dichloromethane-hexane gives cream colored crystals, m.p. 151°-155° C. The preceding compound is reacted with formylhydrazine in refluxing n-butanol for 24 hours to give the product of the example.

Workup

  1. additionA mixture of 7.0 g
  2. customThe solvent is removed
  3. additionice water added to the residue
  4. filtrationFiltration
  5. customgives 7.2 g
  6. customRecrystallization from dichloromethane-hexane
  7. customgives cream colored crystals, m.p. 151°-155° C
  8. customto give the product of the example

Sources & evidence

ORD record
ord-3c3f1b4bdd0b44b9b8a0c33e15f9f045
Source dataset
uspto-grants-1978_09
Patent number
US04112095

Reaction notes

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