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

HRID 1164802

Reaction equation

HRID 1164802 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-8fff56dbcde544d9a17b631b62886d5f
Source dataset
uspto-grants-1990_03
Patent number
US04906628

Linked notes

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