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

HRID 542462Notes

Reaction equation

HRID 542462 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-a907acd692e744f49654c515e093014c
Source dataset
uspto-grants-1987_04
Patent number
US04657906

Reaction notes

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