Dimethylformamide → 4-Amino-N-[4-(5-oxo-4,5-dihydropyrazin-2-yl)phenyl]benzamide

HRID 637488Notes

Reaction equation

HRID 637488 reaction equation
[N+:1]([C:4]1[CH:25]=[CH:24][C:7]([C:8]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[N:18]=[CH:19][C:20](=[O:23])[NH:21][CH:22]=3)=[CH:13][CH:12]=2)=[O:9])=[CH:6][CH:5]=1)([O-])=O.C1CCCCC=1.CN(C)C=O>[Pd].C(O)C>[NH2:1][C:4]1[CH:25]=[CH:24][C:7]([C:8]([NH:10][C:11]2[CH:12]=[CH:13][C:14]([C:17]3[N:18]=[CH:19][C:20](=[O:23])[NH:21][CH:22]=3)=[CH:15][CH:16]=2)=[O:9])=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 8079CyclohexeneHCID 138535664-Nitro-N-(4-(5-oxo-4,5-dihydropyrazin-2-yl)phenyl)benzamide

Product 1

HCID 138535674-Amino-N-[4-(5-oxo-4,5-dihydropyrazin-2-yl)phenyl]benzamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

5-[4-(4-Nitrobenzamido)phenyl]-2(1H)-pyrazinone (1.0 g) was added to a vigorously stirred suspension of palladium on charcoal (0.3 g, 5%) in ethanol (20 ml) followed by cyclohexene (20 ml). The reaction was heated under reflux for 24 hours, hot dimethylformamide was then added and the mixture was filtered. Evaporation of the filtrate gave a solid residue which was extracted with boiling glacial acetic acid, collected and dried to give the title compound (0.6 g, m.p. >300° C.; δ(DMSO-d6) 7.99 and 8.09 (2H, 2s, pyrazinone ring protons), 9.7 and 9.9 (2H, 2 broad s, =CH--NH--CO and --NH--CO).

Workup

  1. temperatureThe reaction was heated
  2. temperatureunder reflux for 24 hours
  3. filtrationthe mixture was filtered
  4. customEvaporation of the filtrate
  5. customgave a solid residue which
  6. extractionwas extracted with boiling glacial acetic acid
  7. customcollected
  8. customdried

Sources & evidence

ORD record
ord-bf40722ab2164da49ef0ec92aa23a7c5
Source dataset
uspto-grants-1985_12
Patent number
US04556711

Reaction notes

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