Phenylhydrazine → HCID 58072519, compound

HRID 1805435Notes

Reaction equation

HRID 1805435 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-72920181c2914a2b95b5864048841f05
Source dataset
uspto-grants-2013_01
Patent number
US08354411B2

Reaction notes

Loading…