Ammonia → 6-[4-(4-Oxo-1,4-dihydropyridin-1-yl)phenyl]-4,5-dihydro-3(2H)-pyridazinone

HRID 5797

Reaction equation

HRID 5797 reaction equation
Cl.[NH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH2:10][CH2:11][C:12](=[O:15])[NH:13][N:14]=2)=[CH:5][CH:4]=1.O1[CH:21]=[CH:20][C:19](=[O:22])[CH:18]=[CH:17]1.N>O>[O:22]=[C:19]1[CH:20]=[CH:21][N:2]([C:3]2[CH:8]=[CH:7][C:6]([C:9]3[CH2:10][CH2:11][C:12](=[O:15])[NH:13][N:14]=3)=[CH:5][CH:4]=2)[CH:17]=[CH:18]1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 79684H-pyran-4-oneHCID 128050056-(4-aminophenyl)-4,5-dihydro-3(2H)-pyridazinone hydrochloride

Product 1

HCID 197942256-[4-(4-Oxo-1,4-dihydropyridin-1-yl)phenyl]-4,5-dihydro-3(2H)-pyridazinone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A stirred mixture of 6-(4-aminophenyl)-4,5-dihydro-3(2H)-pyridazinone hydrochloride (1.5 g), 4H-pyran-4-one (0.7 g), and water (20 ml), was heated under reflux for 41/2 hours. The resultant solid was dissolved in the minimum of hot water and the solution was neutralised with ammonia to give the crude product. Recrystallisation from water gave the title compound, 0.73 g, m.p. 270°-272° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 41/2 hours
  3. customto give the crude product
  4. customRecrystallisation from water

Sources & evidence

ORD record
ord-485e041677a3458f8860e1c73bcd36fb
Source dataset
uspto-grants-1993_09
Patent number
US05246928

Linked notes

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