Phenylhydrazine → HCID 58072519, compound

HRID 2089743Notes

Reaction equation

HRID 2089743 reaction equation
C[N:2](C)[CH:3]=[CH:4][C:5]([C:7]1[C:12](=[O:13])[CH:11]=[CH:10][N:9]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([OH:20])[CH:15]=2)[N:8]=1)=O.[C:22]1([NH:28]N)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>CO>[OH:20][C:16]1[CH:15]=[C:14]([N:9]2[CH:10]=[CH:11][C:12](=[O:13])[C:7]([C:5]3[N:28]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[N:2]=[CH:3][CH:4]=3)=[N:8]2)[CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 7516PhenylhydrazineHCID 66710735HCID 66710735, compound

Product 1

HCID 58072519HCID 58072519, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 3-[3-(dimethylamino)prop-2-enoyl]-1-(3-hydroxyphenyl)pyridazin-4(1H)-one (0.481 g, 1.69 mmol) in methanol (10 mL) was treated with phenylhydrazine (0.462 g, 4.28 mmol) and the resulting mixture was stirred at reflux for 14 h. After this time, the reaction was directly concentrated to remove methanol and then dissolved in methylene chloride (60 mL). The solution was washed with water (60 mL), and brine (20 mL). After concentrated with silica gel, chromatography (silica, methylene chloride to 1:19 methanol/methylene chloride) afforded 1-(3-hydroxyphenyl)-3-(1-phenyl-1H-pyrazol-5-yl)pyridazin-4(1H)-one (0.360 g, 65%) as a brown-yellow solid.

Workup

  1. temperatureat reflux for 14 h
  2. concentrationAfter this time, the reaction was directly concentrated
  3. customto remove methanol
  4. dissolutiondissolved in methylene chloride (60 mL)
  5. washThe solution was washed with water (60 mL), and brine (20 mL)
  6. concentrationAfter concentrated with silica gel, chromatography (silica, methylene chloride to 1:19 methanol/methylene chloride)

Sources & evidence

ORD record
ord-2e44783c179c437483c8096498c1af78
Source dataset
uspto-grants-2013_05
Patent number
US08435995B2

Reaction notes

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