Hydrazine hydrate (1:1) → CID 86697018

HRID 1525399Notes

Reaction equation

HRID 1525399 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-f59f1cbc3f7443bb8b4e54ccacfab19d
Source dataset
uspto-grants-2015_07
Patent number
US09079909B2

Reaction notes

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