Hydrazine hydrate (1:1) → HCID 68536564, compound

HRID 2389315Notes

Reaction equation

HRID 2389315 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=2)[C:9](=O)[CH2:10][CH:11](O)[C:12](OCC)=[O:13])=[CH:4][CH:3]=1.O.[NH2:27][NH2:28]>C(O)CCC>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=2)[C:9]2[CH:10]=[CH:11][C:12](=[O:13])[NH:27][N:28]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 68535649HCID 68535649, compound

Product 1

HCID 68536564HCID 68536564, compoundYield 50.5%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
130 °C

Procedure

To a solution of ethyl 5,5-bis(4-fluorophenyl)-2-hydroxy-4-oxopentanoate (796 mg) in 1-butanol (4 mL) was added hydrazine hydrate (137 mg) at ambient temperature. The reaction mixture was stirred at 130° C. for 12 hours. After cooling to ambient temperature, the reaction mixture was evaporated in vacuo. The resulting residue was stirred at 160° C. for 3 hours. After cooling, the reaction mixture was purified by silica gel column chromatography (EtOAc:n-hexane=2:1) and crystallized from solvent (EtOAc:n-hexane=1:2) to give 6-[bis(4-fluorophenyl)methyl]pyridazin-3(2H)-one (344 mg) as a pale brown solid.

Workup

  1. temperatureAfter cooling to ambient temperature
  2. customthe reaction mixture was evaporated in vacuo
  3. stirringThe resulting residue was stirred at 160° C. for 3 hours
  4. temperatureAfter cooling
  5. customthe reaction mixture was purified by silica gel column chromatography (EtOAc:n-hexane=2:1)
  6. customcrystallized from solvent (EtOAc:n-hexane=1:2)

Sources & evidence

ORD record
ord-d5f447e28adf4d96b31aa4384b02d259
Source dataset
uspto-grants-2012_09
Patent number
US08273745B2

Reaction notes

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