Pyridine → N-[4-(5-Oxo-4,5-dihydropyrazin-2-yl)phenyl]pyridine-4-carboxamide

HRID 637498Notes

Reaction equation

HRID 637498 reaction equation
Br.[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.[N:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.Cl.C(Cl)C1C=CN=CC=1.CN(C)[CH:33]=[O:34]>>[C:33]([NH:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[N:10]=[CH:11][C:12](=[O:15])[NH:13][CH:14]=2)=[CH:7][CH:8]=1)(=[O:34])[C:19]1[CH:20]=[CH:21][N:16]=[CH:17][CH:18]=1

Participants

5

Reactant 4

HCID 1049PyridineHCID 6228Dimethylformamide2×HCID 745704-(Chloromethyl)pyridinium chlorideHCID 202086625-(4-Aminophenyl)-2(1H)-pyrazinone hydrobromide

Product 1

HCID 13853576N-[4-(5-Oxo-4,5-dihydropyrazin-2-yl)phenyl]pyridine-4-carboxamide

Procedure

To a stirred solution of 5-(4-aminophenyl)-2-(1H)-pyrazinone hydrobromide (1.3 g) in dimethylformamide (20 ml) containing pyridine (1 ml) was added a solution of isonicotinyl chloride hydrochloride (1.3 g) in dimethylformamide (10 ml). The mixture was heated under reflux for 4 hours and evaporated to small volume. Water was added to the residue and the solid (1.0 g) was collected, washed with water, dilute sodium hydroxide solution (pH8), water and then dried to give the title compound m.p. 303°-308° C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 4 hours
  3. customevaporated to small volume
  4. additionWater was added to the residue
  5. customthe solid (1.0 g) was collected
  6. washwashed with water, dilute sodium hydroxide solution (pH8), water
  7. customdried

Sources & evidence

ORD record
ord-5dd267cc29a248588a919fa47805da14
Source dataset
uspto-grants-1985_12
Patent number
US04556711

Reaction notes

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