5-(4-Nitrophenyl)pyrazin-2(1H)-one → 5-(4-Aminophenyl)pyrazin-2(1H)-one

HRID 1981379Notes

Reaction equation

HRID 1981379 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:11]=[CH:12][C:13](=[O:16])[NH:14][CH:15]=2)=[CH:6][CH:5]=1)([O-])=O.[H][H]>[Pd].CN(C)C=O>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[N:11]=[CH:12][C:13](=[O:16])[NH:14][CH:15]=2)=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 138535735-(4-Nitrophenyl)pyrazin-2(1H)-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 123580285-(4-Aminophenyl)pyrazin-2(1H)-oneYield 81.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

5-(4-Nitrophenyl)-2-(1H)-pyrazinone (0.1 g) was hydrogenated over 10% Palladium on Charcoal (0.01 g) at atmospheric pressure in 50% aqueous dimethylformamide containing 2N sodium hydroxide (0.46 ml). Once the theoretical quantity of hydrogen uptake had been observed, the reaction mixture was filtered and the filtrate treated with HCl to pH 6 and evaporated. Trituration of the residue with water afforded 5-(4-aminophenyl)-2(1H)-pyrazinone (0.07 g), m.p. 269°-271.5° C. (with decomposition).

Workup

  1. filtrationthe reaction mixture was filtered
  2. additionthe filtrate treated with HCl to pH 6
  3. customevaporated

Sources & evidence

ORD record
ord-2eea52caaa1c4dc3bd3c3b963809bc46
Source dataset
uspto-grants-1985_04
Patent number
US04514568

Reaction notes

Loading…