Hydrazine → HCID 58504230, compound

HRID 2407687Notes

Reaction equation

HRID 2407687 reaction equation
[Cl:1][C:2]1[C:7]2[C:8]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[N:9][O:10][C:6]=2[C:5](Cl)=[N:4][N:3]=1.[NH2:18][NH2:19]>O1CCOCC1.C(O)C>[Cl:1][C:2]1[C:7]2[C:8]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[N:9][O:10][C:6]=2[C:5]([NH:18][NH2:19])=[N:4][N:3]=1

Participants

5

Reactant 2

HCID 9321HydrazineHCID 86659056HCID 86659056, compound

Product 1

HCID 58504230HCID 58504230, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 312751,4-DioxaneSolvent

Procedure

To 4,7-dichloro-3-phenylisoxazolo[4,5-d]pyridazine (25.5 g, Desimoni, G.; Et al. Tetrahedron 1967, 23, 681) in 1,4-dioxane (200 mL) and ethanol (50 mL) at 0° C. was added hydrazine (7.0 g) slowly. The reaction mixture was allowed to slowly warm to room temperature. After 20 hours, the reaction mixture was concentrated and the solid obtained was washed with water and filtered. The material was purified by column chromatography on silica gel (methanol:dichloromethane=5:95) to afford first the regioisomer of the title compound followed by the later eluting title compound (4.50 g) having the following physical data.

Workup

  1. concentrationthe reaction mixture was concentrated
  2. customthe solid obtained
  3. washwas washed with water
  4. filtrationfiltered
  5. customThe material was purified by column chromatography on silica gel (methanol:dichloromethane=5:95)

Sources & evidence

ORD record
ord-1d73331f422b4bd2ac43d6a2511c8918
Source dataset
uspto-grants-2014_08
Patent number
US08809538B2

Reaction notes

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