Hydrazine hydrate (1:1) → CID 86697018

HRID 1775532Notes

Reaction equation

HRID 1775532 reaction equation
Cl[C:2]1[N:3]=[N:4][C:5]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[C:6]([Cl:16])[C:7]=1[C:8]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=O.O.[NH2:24][NH2:25]>C(O)C>[Cl:16][C:6]1[C:5]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[N:4][N:3]=[C:2]2[NH:24][N:25]=[C:8]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[C:7]=12

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 86697016HCID 86697016, compound

Product 1

HCID 86697018CID 86697018Yield 8.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of (3,5-dichloro-6-phenylpyridazin-4-yl)(phenyl)methanone (150 mg, 0.46 mmol) and hydrazine hydrate (27 mg, 0.55 mmol) in ethanol (0.5 mL) was stirred at 40° C. for 1 h in a sealed tube. The reaction mixture was cooled and filtered, and the residue was washed with diethyl ether. The filtrate was concentrated in vacuo. The crude residue was purified by column chromatography (silica gel, gradient 0 to 20% ethyl acetate/isohexane) yielding Compound 9 as a white solid (12 mg).

Workup

  1. temperatureThe reaction mixture was cooled
  2. filtrationfiltered
  3. washthe residue was washed with diethyl ether
  4. concentrationThe filtrate was concentrated in vacuo
  5. customThe crude residue was purified by column chromatography (silica gel, gradient 0 to 20% ethyl acetate/isohexane)

Sources & evidence

ORD record
ord-562f80b272104b9986547d29144a1e81
Source dataset
uspto-grants-2016_02
Patent number
US09260381B2

Reaction notes

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