Hydrochloric Acid → 5-[4-(4-Oxo-1,4-dihydropyridin-1-yl)phenyl]-2(1H)-pyrazinone

HRID 973933

Reaction equation

HRID 973933 reaction equation
Cl.[NH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]=[CH:11][C:12](=[O:15])[NH:13][CH:14]=2)=[CH:5][CH:4]=1.Cl.O1[CH:22]=[CH:21][C:20](=[O:23])[CH:19]=[CH:18]1>O>[O:23]=[C:20]1[CH:21]=[CH:22][N:2]([C:3]2[CH:4]=[CH:5][C:6]([C:9]3[N:10]=[CH:11][C:12](=[O:15])[NH:13][CH:14]=3)=[CH:7][CH:8]=2)[CH:18]=[CH:19]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 79684H-pyran-4-oneHCID 197942325-(4-Aminophenyl)-2(1H)-pyrazinone hydrochloride

Product 1

HCID 197942135-[4-(4-Oxo-1,4-dihydropyridin-1-yl)phenyl]-2(1H)-pyrazinone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A stirred mixture of 5-(4-aminophenyl)-2(1H)pyrazinone hydrochloride (1.5 g, from hydrolysis of the corresponding acetamido derivative with hydrochloric acid) 4H-pyran-4-one (0.71 g) and water (15 ml) was heated under reflux for 21/2 hours under a nitrogen atmosphere. The resultant solution was neutralised to give a solid, 1.79 g, m.p. 345° C. (dec). Recrystallisation from aqueous ethanol gave the title compound. 0.93 g. m.p. 354-357° C. (dec).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 21/2 hours under a nitrogen atmosphere
  3. customto give a solid, 1.79 g, m.p. 345° C. (dec)
  4. customRecrystallisation from aqueous ethanol

Sources & evidence

ORD record
ord-92393c4599934396875828344ae383dc
Source dataset
uspto-grants-1991_11
Patent number
US05066653

Linked notes

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