Hydrochloric Acid → 4,5-Dihydro-5-methyl-6-(4-(4-oxo-1(4H)-pyridinyl)phenyl)-3(2H)-pyridazinone

HRID 1164818Notes

Reaction equation

HRID 1164818 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]([CH3:15])[CH2:10][C:11](=[O:14])[NH:12][N:13]=2)=[CH:4][CH:3]=1.CN(C)[CH:18]=[CH:19][C:20](=[O:26])[CH:21]=[CH:22]N(C)C.Cl>O>[CH3:15][CH:9]1[C:8]([C:5]2[CH:6]=[CH:7][C:2]([N:1]3[CH:22]=[CH:21][C:20](=[O:26])[CH:19]=[CH:18]3)=[CH:3][CH:4]=2)=[N:13][NH:12][C:11](=[O:14])[CH2:10]1

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 161928Ici 109,081HCID 534218661,5-Bis(dimethylamino)penta-1,4-dien-3-one

Product 1

HCID 1307024,5-Dihydro-5-methyl-6-(4-(4-oxo-1(4H)-pyridinyl)phenyl)-3(2H)-pyridazinone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 6-(4-aminophenyl)-5-methyl-4,5-dihydro-3(2H)-pyridazinone (101 mg), 1,5-bis(dimethylamino)-1,4-pentadien-3-one (84 mg) and hydrochloric acid (1N, 0.5 ml) in water (1.5 ml) was stirred at room temperature for 4 hours. More hydrochloric acid (1N, 0.5 ml) was added and the reaction mixture was stirred at room temperature for 18 hours and then under reflux for 4 hours to afford a quantity of red insoluble material. The hot aqueous solvent was decanted off from the insoluble material, was allowed to cool and was seeded to afford the title compound, 41 mg, m.p. 245°-249° C.

Workup

  1. stirringthe reaction mixture was stirred at room temperature for 18 hours
  2. temperatureunder reflux for 4 hours
  3. customto afford a quantity of red insoluble material
  4. customThe hot aqueous solvent was decanted off from the insoluble material
  5. temperatureto cool

Sources & evidence

ORD record
ord-10877a1c2c834c578f6c680e72aa5449
Source dataset
uspto-grants-1990_03
Patent number
US04906628

Reaction notes

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